1448189-28-3|2-(Trimethylsilyl)ethyl (4-bromobenzyl)carbamate| Ambeed

Yield	Reaction Conditions	Operation in experiment
44%	With bis(tri-t-butylphosphine)palladium(0); ammonium chloride; caesium carbonate; In N,N-dimethyl-formamide; at 170℃; for 0.266667h;Microwave irradiation;	2-(trimethylsilyl)ethyl 4-(4-methylthiazol-5-yl)benzylcarbamate - tr met y s y et y 4-bromobenzylcarbamate (132 mg, 0.4 mmol, 1 eq), 4- methylthiazole-5-carboxylic acid (114.5 mg, 0.8 mmol, 2 eq), tetrabutylammonium chloride hydrate (118 mg, 0.4 mmol, 1 eq), cesium carbonate (196 mg, 0.6 mmol, 1.5 eq) and Pd(P(tBu)3)2 (40.8 mg, 0.08 mmol, 0.2 eq) were dissolved in DMF (4 mL).1 The reaction was heated to 170°C in a microwave reactor for 16 minutes. The mixture was then cooled to room temperature, diluted with EtOAc and washed thrice with brine, once with saturated sodium bicarbonate, water, and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by coulm chromatography (10 to 35percent EtOAc/hexanes) gave a colorless oil (61.7 mg, 0.177 mmol, 44percent). NMR (400 MHz, CDCI3) delta 8.67 (s, 1H), 7.43 - 7.37 (m, 2H), 7.34 (d, J= 8.1 Hz, 2H), 5.09 (s, 1H), 4.39 (d, J= 6.0 Hz, 2H), 4.28 - 4.02 (m, 2H), 2.52 (s, 3H), 1.10 - 0.90 (m, 2H), 0.14 - -0.09 (m, 9H). 13C NMR (101 MHz, CDC13) delta 156.98, 150.42, 148.66, 138.76, 131.67, 131.18, 129.66, 127.89, 63.46, 44.71, 17.90, 16.18, -1.34. MS (ESI) 349.0 (M+H).
44%	With bis(tri-t-butylphosphine)palladium(0); tetrabutylammonium chloride hydrate; caesium carbonate; In N,N-dimethyl-formamide; at 170℃; for 0.266667h;Microwave irradiation;	2-(trimethylsilyl)ethyl 4-bromobenzylcarbamate (132 mg, 0.4 mmol, 1 eq), <strong>[20485-41-0]4-methylthiazole-5-carboxylic acid</strong> (114.5 mg, 0.8 mmol, 2 eq), tetrabutylammonium chloride hydrate (118 mg, 0.4 mmol, 1 eq), cesium carbonate (196 mg, 0.6 mmol, 1.5 eq) and Pd(P(tBu)3)2 (40.8 mg, 0.08 mmol, 0.2 eq) were dissolved in DMF (4 mL).1 The reaction was heated to 170° C. in a microwave reactor for 16 minutes. The mixture was then cooled to room temperature, diluted with EtOAc and washed thrice with brine, once with saturated sodium bicarbonate, water, and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (10 to 35percent EtOAc/hexanes) gave a colorless oil (61.7 mg, 0.177 mmol, 44percent). 1H NMR (400 MHz, CDCl3) delta 8.67 (s, 1H), 7.43-7.37 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 5.09 (s, 1H), 4.39 (d, J=6.0 Hz, 2H), 4.28-4.02 (m, 2H), 2.52 (s, 3H), 1.10-0.90 (m, 2H), 0.14-0.09 (m, 9H). 13C NMR (101 MHz, CDCl3) delta 156.98, 150.42, 148.66, 138.76, 131.67, 131.18, 129.66, 127.89, 63.46, 44.71, 17.90, 16.18, ?1.34. MS (ESI) 349.0 (M+H).
44%	With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); tetrabutyl-ammonium chloride; caesium carbonate; In N,N-dimethyl-formamide; at 170℃; for 0.266667h;Microwave irradiation;	2-(trimethylsilyl)ethyl 4-(4-methylthiazol-5-yl)benzylcarbamate 2-(Trimethylsilyl)ethyl 4-bromobenzylcarbamate (132 mg, 0.4 mmol, 1 eq), <strong>[20485-41-0]4-methylthiazole-5-carboxylic acid</strong> (114.5 mg, 0.8 mmol, 2 eq), tetrabutylammonium chloride hydrate (118 mg, 0.4 mmol, 1 eq), cesium carbonate (196 mg, 0.6 mmol, 1.5 eq) and Pd(P(tBu)3)2 (40.8 mg, 0.08 mmol, 0.2 eq) were dissolved in DMF (4 mL). The reaction was heated to 170° C. in a microwave reactor for 16 minutes. The mixture was then cooled to room temperature, diluted with EtOAc and washed thrice with brine, once with saturated sodium bicarbonate, water, and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (10 to 35percent EtOAc/hexanes) gave a colorless oil (61.7 mg, 0.177 mmol, 44percent). 1H NMR (400 MHz, CDCl3) delta 8.67 (s, 1H), 7.43-7.37 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 5.09 (s, 1H), 4.39 (d, J=6.0 Hz, 2H), 4.28-4.02 (m, 2H), 2.52 (s, 3H), 1.10-0.90 (m, 2H), 0.14-0.09 (m, 9H). 13C NMR (101 MHz, CDCl3) delta 156.98, 150.42, 148.66, 138.76, 131.67, 131.18, 129.66, 127.89, 63.46, 44.71, 17.90, 16.18, -1.34. MS (ESI) 349.0 (M+H).

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2-(Trimethylsilyl)ethyl (4-bromobenzyl)carbamate

CAS No.: 1448189-28-3

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[ 1448189-28-3 ] Synthesis Path-Downstream 1~1

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