Dimethylformamide → 4-(4-Amino-3-fluorophenoxy)-7-oxiranylmethoxyquinoline-6-carbonitrile

HRID 387947Notes

Reaction equation

HRID 387947 reaction equation
CN(C)C=O.[CH2:6]([CH:8]1[O:10][CH2:9]1)Br.C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[CH:37]=[CH:36][C:21]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([OH:35])=[C:30]([C:33]#[N:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)=[CH:20][C:19]=1[F:38]>C(OCC)(=O)C.O>[NH2:17][C:18]1[CH:37]=[CH:36][C:21]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:6][CH:8]4[CH2:9][O:10]4)=[C:30]([C:33]#[N:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)=[CH:20][C:19]=1[F:38]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1358293794-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline

Product 1

HCID 229362494-(4-Amino-3-fluorophenoxy)-7-oxiranylmethoxyquinoline-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding dimethylformamide (6 ml), epibromohydrin (1.3 ml) and potassium carbonate (380 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (400 mg), the mixture was stirred overnight at room temperature. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (400 mg).

Workup

  1. washthe organic layer was washed with water and saturated saline in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0ef93cf0dc4c4b6494bc9ae5e084e1a6
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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