185950-64-5|(5-Chloro-2-pivalamidophenyl)boronic acid| Ambeed

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CAS No. :	185950-64-5
Formula :	C₁₁H₁₅BClNO₃
M.W :	255.51
SMILES Code :	CC(C)(C)C(NC1=CC=C(Cl)C=C1B(O)O)=O
MDL No. :	MFCD01114875

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Yield	Reaction Conditions	Operation in experiment
		N-(4-Chloro-phenyl)-2,2-dimethyl-propionamide (2.11 g, 10 mmol) was dissolved in anhydrous THF (25 mL) and cooled to 0 C., then n-butyl lithium (22 mmol, 8.8 mL of 2.5 M solution in hexanes) was added dropwise over 30 minutes. The reaction mixture was stirred at this temperature for an additional 2 h and was then cooled to -78 C. A solution of trimethylborate (3.11 g, 30 mmol) in anhydrous THF was added and the mixture was allowed to warm to room temperature and stirred overnight. After concentrating by rotary evaporation the crude product was acidified with 3NHCl. The crystalline solid was collected by filtration, washed with water and dried to afford 1.2 g of the boronic acid MS: MS (M+H+): 256.
		Scheme XI: General procedure for the synthesis of biarylamines; [00420] N- (4-Chloro-phenyl)-2,2-dimethyl-propionamide g, 10 mmol) was dissolved in anhydrous THF (25 mL) and cooled to 0 C , then n-butyl lithium (22 mmol, 8.8 mL of 2.5 M solution in hexanes) was added dropwise over 30 minutes. The reaction mixture was stirred at this temperature for an additional 2 h and was then cooled to-78 C. A solution of trimethylborate (3.11 g, 30 mmol) in anhydrous THF was added and the mixture was allowed to warm to room temperature and stirred overnight. After concentrating by rotary evaporation the crude product was acidified with 3N HCI. The crystalline solid was collected by filtration, washed with water and dried to afford 1.2 g of the boronic acid MS: MS (M+H+): 256. The boronic acid (0.5 mmol), the appropriate aryl halide (0.5 mmol), tetrakis(triphenylphosophine)palladium(0) (0.025 mmol) and K2C03 (1 mmol) were suspended DMF (5 mL) and heated at 100 C overnight. After cooling to room temperature the reaction mixture was diluted with ether (20 mL) and washed twice with 10 mL portions of water. The organic extract was concentrated and product was purified by flash chromatography on silica gel column using 5-20% ethylacetate/hexane solvent mixture. The pivaloyl protected biaryl was suspended in 70% sulfuric acid and refluxed overnight. After cooling to room temperature the reaction was cautiously added to cold concentrated aqueous NaOH solution to achieve neutral pH and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated to afford product. 4-Chloro-2-pvridin-2-vl-phenylamine [00421] The title compound was prepared according to the general procedure described in Scheme XI using 2-chloropyridine as the aryl halide component. MS: (M+H)/z = 205.

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CAS No.: 185950-64-5

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CAS No.: 185950-64-5

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[ 185950-64-5 ] Synthesis Path-Downstream 1~1

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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed