Water → N-ethyl-3-fluoro-5-(1H-indazol-6-yl)-4-methylbenzamide

HRID 2246624Notes

Reaction equation

I[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:11]([NH:13][C:14]([C:16]1[CH:17]=[C:18]([F:26])[C:19]([CH3:25])=[C:20](B(O)O)[CH:21]=1)=[O:15])[CH3:12].C(=O)([O-])O.[Na+].O>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([NH:13][C:14](=[O:15])[C:16]1[CH:21]=[C:20]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[CH:4][CH:3]=2)[C:19]([CH3:25])=[C:18]([F:26])[CH:17]=1)[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 6-iodo-1H-indazole (0.5 g, {5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (Intermediate 17, 0.56 g), tetrakis(triphenylphosphine)palladium(0) (0.05 g) and aqueous sodium hydrogen carbonate (1M, 1 ml) in isopropanol (10 ml) was heated at 150° C. for 30 min in a microwave oven. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate (3×20 ml). The extracts were dried (Na2SO4) and concentrated under vacuum. The residual oil was purified by column chromatography on silica (50 g) eluting with ether/ethyl acetate (4:1). The resultant product was triturated with a small quantity of dichloromethane to give the title compound as a pale yellow solid (0.15 g).

Workup

extractionextracted with ethyl acetate (3×20 ml)
dry with materialThe extracts were dried (Na2SO4)
concentrationconcentrated under vacuum
customThe residual oil was purified by column chromatography on silica (50 g)
washeluting with ether/ethyl acetate (4:1)
customThe resultant product was triturated with a small quantity of dichloromethane

Sources & evidence

ORD record: ord-05256219ea59472a92c12c4cc87e9ac1
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687532B2

Reaction notes

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