Sodium Bicarbonate → HCID 178464760, compound

HRID 2246633Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:15][CH2:14][O:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:16]([NH:18][C:19](=[O:36])[C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[C:23]([CH3:35])=[CH:22][CH:21]=1)[CH3:17].C(=O)([O-])O.[Na+]>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>[CH2:16]([NH:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][C:23]([CH3:35])=[C:22]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH:11]4[CH2:15][CH2:14][O:13][CH2:12]4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:21]=1)[CH3:17]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-bromo-3-(tetrahydro-3-furanyl)-1H-indazole (Intermediate 9, 84 mg) N-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate, 10, 91 mg) aqueous sodium hydrogen carbonate (1M, 630 μL) and tetrakis(triphenylphosphine)palladium(0) (7 mg) in isopropanol (4 ml) in a sealed vial was stirred at 150° C. for 15 min in a microwave oven. The solvent was removed under vacuum and the residue was purified by chromatography on a silica column, eluting with a cyclohexane:ethyl acetate gradient, to give the title compound as a white solid (36 mg).

Workup

customThe solvent was removed under vacuum
customthe residue was purified by chromatography on a silica column
washeluting with a cyclohexane

Sources & evidence

ORD record: ord-9d5d1c081c2f474387ce74b3f480f077
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687532B2

Reaction notes

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