2-Chlorobenzoyl chloride → HCID 22627283, compound

HRID 1108741Notes

Reaction equation

[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:25][CH2:26][CH3:27])(=[O:5])[CH:2]([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[Cl:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40](Cl)=[O:41]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH:10]=2)[C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[C:7]1[CH2:25][CH2:26][CH3:27])=[O:41]

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred mixture of benzyl 3-isobutyryl-2-propylindole-6-carboxylate (207 mg) and diisopropylethylamine (295 mg) in dichloromethane (6 ml) were added 2-chlorobenzoyl chloride (299 mg) and 4-dimethylaminopyridine (12 mg) at 0° C. The reaction mixture was refluxed for 15 hours. The reaction mixture was cooled to 20° C. and washed with 1N hydrochloric acid, water, saturated sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:10) to give benzyl 1-(2-chlorobenzoyl)-3-isobutyryl-2-propylindole-6-carboxylate (330 mg) as yellow crystals.

Workup

temperatureThe reaction mixture was refluxed for 15 hours
washwashed with 1N hydrochloric acid, water, saturated sodium bicarbonate, water and brine
dry with materialThe organic phase was dried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:10)

Sources & evidence

ORD record: ord-b676817f573d48e0a4f88c24529d5791
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

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