2,5-Dichlorobenzoyl chloride → HCID 23288159, compound

HRID 367425Notes

Reaction equation

HRID 367425 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.[Cl:19][C:20]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:21]=1[C:22](Cl)=[O:23].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Cl:19][C:20]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:21]=1[C:22]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][C:9]=2[F:11])[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=2)=[CH:6]1)=[O:23]

Participants

5

Reactant 3

HCID 179452,5-Dichlorobenzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 23288108HCID 23288108, compound

Product 1

HCID 23288159HCID 23288159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5.6 mg, 33%); from 5,7-difluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4g, 10 mg, 0.04 mmol) and 2,5-dichlorobenzoyl chloride (12.6 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-23d16c6cb4fa418f90985cc8417356d6
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

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