2-Chlorobenzoyl chloride → HCID 22627283, compound

HRID 278126Notes

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 or 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
additionsilica gel eluting with a mixture of ethyl acetate and hexane (1:10)

Sources & evidence

ORD record: ord-5bc2c9462baf478e857abda514d5ee6f
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358992B1

Reaction notes

Loading…