Dichloromethane → 7-Fluoro-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17499

Reaction equation

HRID 17499 reaction equation
Cl.[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C(N(CC)CC)C.ClCCl.[NH2:20][C:21]1[C:26]([OH:27])=[C:25]([F:28])[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:22]=1[C:36]#[N:37]>C(OCC)(=O)C>[F:28][C:25]1[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:22]([C:36]#[N:37])=[C:21]2[C:26]=1[O:27][C:2]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=[N:20]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 685843947-Fluoro-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Nicotinyl chloride hydrochloride (192 mg, 1.08 mmol) and triethylamine (301 μl, 2.16 mmol) were added to a dichloromethane (9 ml) solution of 4-amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (218 mg, 0.900 mmol), followed by stirring at room temperature for 2 hours. Ethyl acetate (100 ml) was added to the reaction liquid, followed by washing with water (50 ml) and saturated brine (50 ml).

Workup

  1. washby washing with water (50 ml) and saturated brine (50 ml)

Sources & evidence

ORD record
ord-b06515a8803d431d872f27a069688415
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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