Water → 1,1-Dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-1-piperazinecarboxylate

HRID 2246632Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:24]([NH:26][C:27](=[O:45])[C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[C:31]([CH3:43])=[C:30]([F:44])[CH:29]=1)[CH3:25].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.C(Cl)Cl>[CH2:24]([NH:26][C:27]([C:28]1[CH:29]=[C:30]([F:44])[C:31]([CH3:43])=[C:32]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([N:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:33]=1)=[O:45])[CH3:25]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1,1-dimethylethyl 4-(6-bromo-1H-indazol-3-yl)-1-piperazinecarboxylate (Intermediate 6, 28 mg), N-ethyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5, 27 mg), tetrakis(triphenylphosphine)palladium (2 mg) and aqueous sodium hydrogen carbonate (0.125 ml) in isopropanol (0.5 ml) was heated at 150° C. in a microwave oven for 15 min. Water and DCM were added and the organic phase was separated using a hydrophobic filter tube. The solvent was evaporated and the residue was purified by reverse phase preparative HPLC to give the title compound (16 mg).

Workup

customthe organic phase was separated
customThe solvent was evaporated
customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-96af7a04149c474fa92170fcf0d5ff86
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687532B2

Reaction notes

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