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Water → (RS)-2-(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-ylmethyl)-benzofuran-3-carbonitrile

HRID 2077340
Notes
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Reaction equation

HRID 2077340 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:18]([C:20]1[N:21]=[C:22]([CH3:32])[S:23][C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:19].[Cu][C:34]#[N:35].O.C(OCC)(=O)C>CN1CCCC1=O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2[S:23][C:22]([CH3:32])=[N:21][C:20]=2[C:18]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[CH2:11][C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[C:34]#[N:35])=[O:19])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23146338(RS)-1-[2-(3-bromo-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 23146262(RS)-2-(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-ylmethyl)-benzofuran-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To (RS)-1-[2-(3-bromo-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone, E81 (270 mg, 0.53 mmol) in N-methyl-pyrrolidinone (8 ml) was added copper(I)cyanide (96 mg, 1.06 mmol) and the mixture stirred under argon at reflux for 6 h. The reaction mixture was cooled, poured into water (80 ml) and ethyl acetate (50 ml) and then filtered through kieselguhr. The filtrate was separated and the aqueous phase extracted with ethyl acetate (2×). The combined organics were washed with water (4×50 ml), dried and the solvent removed in vacuo. Chromatography (silica gel) afforded the title compound as a white amorphous solid (94 mg, 39%).

Workup

  1. temperatureat reflux for 6 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through kieselguhr
  4. customThe filtrate was separated
  5. extractionthe aqueous phase extracted with ethyl acetate (2×)
  6. washThe combined organics were washed with water (4×50 ml)
  7. customdried
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dd53ec6dbd4b4a80adbed256959f5da5
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928124B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes