Water → HCID 60133233, compound

HRID 2246619Notes

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](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=1)[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:31])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:16]=1)[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 6-iodo-1H-indazole (0.45 g), N-ethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 0.54 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 (50 ml) and extracted with ethyl acetate (3×25 ml). The extracts were washed with water (25 ml) dried (Na2SO4) and concentrated under vacuum. The residual oil was purified by column chromatography on silica (50 g) eluting with ether/ethyl acetate (7:3) to give the title compound as a pale yellow foam (0.25 g).

Workup

extractionextracted with ethyl acetate (3×25 ml)
washThe extracts were washed with water (25 ml)
dry with materialdried (Na2SO4)
concentrationconcentrated under vacuum
customThe residual oil was purified by column chromatography on silica (50 g)
washeluting with ether/ethyl acetate (7:3)

Sources & evidence

ORD record: ord-8ce90d8d807246a2ba95ce223afebe35
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687532B2

Reaction notes

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