4-Fluorobenzoyl chloride → HCID 23288095, compound

HRID 367424Notes

Reaction equation

HRID 367424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=1)[CH:6]=[C:5]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 23288108HCID 23288108, compound

Product 1

HCID 23288095HCID 23288095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(6.3 mg, 42%); from 5,7-difluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4g, 10 mg, 0.04 mmol) and 4-fluorobenzoyl chloride (9.5 mg, 0.06 mmol) with 1M NaN(TMS)2 (60 μL, 0.06 mmol) in THF (0.5 mL) at RT.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-e6c949c6b8624695b73f02c2c272255a
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

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