Sodium Bicarbonate → HCID 58830629, compound

HRID 2353396Notes

Reaction equation

Br[C:2]1[C:10]([F:11])=[CH:9][C:8](Br)=[C:7]2[C:3]=1[C:4]([C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)=[N:5][NH:6]2.BrC1C=C2C(C(C3C=NC(OC)=CC=3)=NN2)=CC=1F.[CH2:40]([NH:42][C:43](=[O:60])[C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:45]=1)[CH3:41].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>[CH2:40]([NH:42][C:43](=[O:60])[C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[C:46]([C:9]2[CH:8]=[C:7]3[C:3]([C:4]([C:13]4[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=4)=[N:5][NH:6]3)=[CH:2][C:10]=2[F:11])[CH:45]=1)[CH3:41]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4,7-dibromo-5-fluoro-3-[6-(methyloxy)-3-pyridinyl]-1H-indazole and 6-bromo-5-fluoro-3-[6-(methyloxy)-3-pyridinyl]-1H-indazole (2:1) (Intermediate 9, 20 mg), N-ethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 32 mg), 1M aqueous sodium bicarbonate (1 ml) and tetrakis(triphenylphosphine)palladium (6 mg) in isopropanol was heated in a sealed vessel by microwave at 150° C. for 15 min. The reaction mixture was partitioned between chloroform and water and the organic layer was separated using a hydrophobic filter tube. The organic layer was concentrated under vacuum and the residue was purified by reverse phase preparative HPLC to give the title compound (3 mg).

Workup

customThe reaction mixture was partitioned between chloroform and water
customthe organic layer was separated
concentrationThe organic layer was concentrated under vacuum
customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-a3778f0022dc44198930a1d42f7ed7b0
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750026B2

Reaction notes

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