Isobutyryl chloride → N-[2-[1-(4-fluorophenyl)indazol-5-yl]oxy-2-phenyl-acetyl]-2-methyl-propanamide

HRID 13168Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19]([NH2:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[CH3:34][CH:35]([CH3:39])[C:36](Cl)=[O:37]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:19]([NH:21][C:36](=[O:37])[CH:35]([CH3:39])[CH3:34])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 2-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-2-phenylacetamide (137b, 20 mg, 60 μmol) in THF (2 ml) was cooled to 0° C., and potassium 2-methylpropan-2-olate (18.6 mg, 170 μmol) was added. The mixture was stirred at 0° C. for 10 min, and a solution of 2-methylpropanoyl chloride (30 mg, 280 μmol) in THF (0.5 ml) was added. Stirring was continued for 30 min at 0° C. Then the sample was concentrated in vacuo and purified by semi-prep. HPLC go give white solid material, 14 mg (59%).

Workup

stirringStirring
waitwas continued for 30 min at 0° C
concentrationThen the sample was concentrated in vacuo
custompurified by semi-prep
customHPLC go give white solid material, 14 mg (59%)

Sources & evidence

ORD record: ord-1dcee2700c794235bf9cec9a0d7abf27
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728030B2

Reaction notes

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