Propionyl chloride → 3-[6-Chloro-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl]-benzoic acid ethyl ester

HRID 1466948Notes

Reaction equation

[C:1](Cl)(=O)[CH2:2][CH3:3].[CH2:6]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][C:17]2[C:25]3[C:20](=[C:21]([F:27])[C:22]([Cl:26])=[CH:23][CH:24]=3)[N:19]([C:28](=[NH:31])[NH:29][OH:30])[C:18]=2[CH3:32])[CH:11]=1)[CH3:7]>N1C=CC=CC=1>[CH2:6]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][C:17]2[C:25]3[C:20](=[C:21]([F:27])[C:22]([Cl:26])=[CH:23][CH:24]=3)[N:19]([C:28]3[N:31]=[C:1]([CH2:2][CH3:3])[O:30][N:29]=3)[C:18]=2[CH3:32])[CH:11]=1)[CH3:7]

Participants

Conditions

Temperature: 80 °C

Procedure

Propionyl chloride (0.042 mL, 0.48 mmol) was added to a solution of 3-[6-Chloro-7-fluoro-1-(N-hydroxycarbamimidoyl)-2-methyl-1H-indol-3-ylsulfanyl]-benzoic acid ethyl ester (0.12 g, 0.24 mmol) in pyridine (2 mL) at room temperature. The resulting mixture was heated to 80° C. and stirred for overnight, then cooled to room temeperature and subjected to standard aqueous workup. The crude residue was purified on silica gel (0-60% EtOAc in hexanes) to afford the title compound.

Workup

temperaturecooled to room temeperature
customThe crude residue was purified on silica gel (0-60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-447185436aba4fadaa15fa742749b716
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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