Sodium Bicarbonate → HCID 58830635, compound

HRID 2353397Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[N:7][NH:8]2)=[CH:4][C:3]=1[F:18].[CH2:19]([NH:21][C:22](=[O:39])[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1)[CH3:20].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>[Cl:17][C:14]1[N:13]=[CH:12][C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([C:25]4[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=4[CH3:29])[C:22]([NH:21][CH2:19][CH3:20])=[O:39])=[C:3]([F:18])[CH:4]=3)[NH:8][N:7]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-bromo-3-(6-chloro-3-pyridinyl)-5-fluoro-1H-indazole (Intermediate 12, 16 mg), N-ethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 15 mg), 1M aqueous sodium bicarbonate (1 ml) and tetrakis(triphenylphosphine)palladium (0) (6 mg) in isopropanol (1 ml) was heated at 150° C. for 15 mins in a microwave oven. The reaction mixture was partitioned between chloroform and water and the organic layer separated via hydrophobic filter tube. The organic layer was evaporated and purified by mass directed preparative HPLC to give the title compound 1.64 mg.

Workup

customThe reaction mixture was partitioned between chloroform and water
customthe organic layer separated via hydrophobic filter tube
customThe organic layer was evaporated
custompurified by mass

Sources & evidence

ORD record: ord-5037264fe89c423fb43fbc906da77499
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750026B2

Reaction notes

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