Sodium hydride → 1-(3-Bromo-4-fluorobenzoyl)-3-[2-(2-cyclohexylmethylpiperidino)-ethyl]-5-methoxy-2-methylindole

HRID 2397492Notes

Reaction equation

HRID 2397492 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[NH:18][C:17]=2[CH3:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Na].[Br:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35](Cl)=[O:36]>CN(C=O)C>[Br:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35]([N:18]1[C:19]2[C:24](=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:16]([CH2:15][CH2:14][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]2[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:17]1[CH3:27])=[O:36]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 5360545SodiumHCID 213133653-[2-(2-Cyclohexylmethylpiperidino)ethyl]-5-methoxy-2-methylindole

Product 1

HCID 213133481-(3-Bromo-4-fluorobenzoyl)-3-[2-(2-cyclohexylmethylpiperidino)-ethyl]-5-methoxy-2-methylindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Bromo-4-fluorobenzoyl)-3-[2-(2-cyclohexylmethylpiperidino)-ethyl]-5-methoxy-2-methylindole is prepared by reaction of 3-[2-(2-cyclohexylmethylpiperidino)ethyl]-5-methoxy-2-methylindole with sodium hydride in DMF and reaction of the resulting sodium salt with 3-bromo-4-fluorobenzoyl chloride following the procedure described above in Example 1.

Sources & evidence

ORD record
ord-91a69c4c0a9944a8b1550a3625040584
Source dataset
uspto-grants-1977_05
Patent number
US04021431

Reaction notes

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