METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97 synthesis
- Product Name:METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97
- CAS Number:913836-22-3
- Molecular formula:C5H4BrNO2S
- Molecular Weight:222.06
850429-60-6
913836-22-3
General procedure for the synthesis of methyl 5-bromo-4-thiazolecarboxylate from methyl 2-amino-5-bromothiazole-4-carboxylate: Methyl 2-amino-5-bromothiazole-4-carboxylate (1.0 equiv, 100 mg, 0.42 mmol) was dissolved in anhydrous DMF (0.8 mL). The reaction mixture was heated to 80 °C under nitrogen protection. A solution of tert-butyl nitrite (1.2 eq, 60 μL, 0.50 mmol) in DMF (0.8 mL) was slowly added dropwise to the hot solution. After several minutes of reaction, no gas escaped indicating completion of the reaction. The reaction mixture was cooled to room temperature and then sampled directly onto a preloaded silica gel column. Rapid column chromatographic separation was carried out sequentially using hexane and ethyl acetate/hexane (2:8, v/v) as eluents to afford methyl 5-bromothiazole-4-carboxylate as a yellow solid (49 mg, 53% yield). The product was analyzed by LCMS (ES) showing a purity of 95%, m/z 222 [M]+, 224 [M+2]+.
850429-60-6
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$30.00/1 g
913836-22-3
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$16.00/250mg
Yield: 53%
Reaction Conditions:
with tert.-butylnitrite in N,N-dimethyl-formamide at 80;
Steps:
3.1
Methyl 2-amino-4-bromothiazole-4-carboxylate (1.0 eq, 100 mg, 0.42 mmol) was dissolved in anhydrous DMF (0.8 ml). The mixture was heated to 800C under nitrogen atmosphere. To the hot mixture, a solution of fe?t-Butyl nitrite (1.2 eq, 60 ul, 0.50 mmol) in DMF (0.8 ml) was added dropwise. After a few minutes, absence of gas evolution indicated completion of the reaction. The mixture was cooled down and poured onto a prepacked silica gel column. Flash chromatography using hexanes, then AcOEt/hexanes (2:8), provided methyl 5-bromothiazole-4-carboxylate as a yellow solid (49 mg, 53% yield). LCMS (ES): 95% pure, m/z 222 [M]+, 224 [M+2]+.
References:
CYLENE PHARMACEUTICALS, INC. WO2008/28168, 2008, A2 Location in patent:Page/Page column 157