4-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde → 3-[1-[4-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepin-2-yl]-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

HRID 1839833Notes

Reaction equation

HRID 1839833 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[NH:19][C:20]([CH:22]=O)=[CH:21][C:13]2=3)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH2:33][C:34](=[O:40])[NH:35]3)[CH:28]=[CH:29][CH:30]=1>N1CCCCC1.C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[NH:19][C:20](/[CH:22]=[C:33]4\[C:34](=[O:40])[NH:35][C:36]5[C:32]\4=[C:31]([C:27]4[CH:28]=[CH:29][CH:30]=[C:25]([F:24])[CH:26]=4)[CH:39]=[CH:38][CH:37]=5)=[CH:21][C:13]2=3)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 225617494-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehydeHCID 225617564-(3-Fluoro-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 225617763-[1-[4-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepin-2-yl]-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-oneYield 53.9%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-(1-Acetyl-piperidine-4-carbonyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine-2-carbaldehyde (56 mg) was condensed with 4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one (40 mg) and piperidine (2 drops) in ethanol (1 mL) at rt for overnight. The solvent was concentrated and the residue was purified on a silica gel column to give 50 mg of the title compound as a yellow solid.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-bad46d756dc94eb5b28da35a8c992790
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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