Potassium Iodide → HCID 11998781, compound

HRID 2102738Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([CH:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2([CH2:30][C:29]3[CH:32]=[CH:33][CH:34]=[C:27]([Cl:26])[CH:28]=3)[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of rac-4-(6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-azepane-1-carboxylic acid tert-butyl ester (0.3 g, 0.82 mmol) (from Example 61b supra), 3-chlorobenzyl bromide (0.20 g, 0.97 mmol) (Aldrich), potassium iodide (0.16 g, 0.98 mmol) and potassium carbonate (0.24 g, 1.77 mmol) in acetone (5 mL) was heated at 50° C. for overnight The solvent was removed. The residue was purified by chromatography to give rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-azepane-1-carboxylic acid tert-butyl ester as white solid. (Yield 50 mg, 12.5%).

Workup

customwas removed
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-96e727905ebb4986bac2e19144eab43c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576082B2

Reaction notes

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