Sodium Bicarbonate → HCID 11338162, compound

HRID 2353392Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:7][NH:8]2)=[CH:4][C:3]=1[F:17].[CH:18]1([NH:21][C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=2)[CH2:20][CH2:19]1.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>[CH:18]1([NH:21][C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([C:2]3[CH:10]=[C:9]4[C:5]([C:6]([C:11]5[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=5)=[N:7][NH:8]4)=[CH:4][C:3]=3[F:17])[CH:24]=2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-bromo-5-fluoro-3-(4-pyridinyl)-1H-indazole (Intermediate 4, 20 mg), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (21 mg), tetrakis(triphenylphosphine)palladium(0) (2 mg) and aqueous sodium hydrogen carbonate (1M, 1 ml) in isopropanol (2 ml) was stirred in a microwave oven at 150° C. for 15 min. The mixture was partitioned between water and ethyl acetate and the organic layer was washed with water and brine, dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified on an SPE cartridge (silica, 5 g) eluting with cyclohexane:ethyl acetate (1:1 to 1:4) to give the title compound as a white solid (9.72 mg).

Workup

customThe mixture was partitioned between water and ethyl acetate
washthe organic layer was washed with water and brine
customdried
concentrationconcentrated under vacuum
customThe residue was purified on an SPE cartridge (silica, 5 g)
washeluting with cyclohexane:ethyl acetate (1:1 to 1:4)

Sources & evidence

ORD record: ord-8c8f4533625e44478b2fb1fe0904bd21
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750026B2

Reaction notes

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