Acetyl chloride → 4-(Acetylamino)-3-(4-chlorophenoxy)-2-methyl-1H-indole-1-acetic acid, 1,1-dimethylethyl ester

HRID 2233746Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[C:5]([CH3:19])[N:6]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>CC#N>[C:35]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([O:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)=[C:5]([CH3:19])[N:6]2[CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product from example 3 step (iv) (70 mg) in MeCN (1 ml) was added triethylamine (50 μl) and acetyl chloride (17 μl) and the reaction stirred at 50° C. for 3 h. The residue was partitioned between diethylether/water, the organics were separated, washed with aq potassium hydrogensulfate solution, brine, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-30% ethylacetate/iso-hexane.

Workup

customThe residue was partitioned between diethylether/water
customthe organics were separated
washwashed with aq potassium hydrogensulfate solution, brine
customdried
customevaporated under reduced pressure
customThe residue was purified by chromatography on silica eluting with 5-30% ethylacetate/iso-hexane

Sources & evidence

ORD record: ord-f0bf1411141a4b99845b93cf59c871a3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709521B2

Reaction notes

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