Benzene, 1-bromo-3-(trifluoromethyl)- → 6-(1,6-dimethyl-3-(3-(trifluoromethyl)phenylamino)-1H-indazol-7-yl)-N-methylquinazolin-2-amine

HRID 2092287Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.CC(C)([O-])C.[Na+].[NH2:18][C:19]1[C:27]2[C:22](=[C:23]([C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][CH:38]=3)[N:35]=[C:34]([NH:39][CH3:40])[N:33]=[CH:32]4)[C:24]([CH3:28])=[CH:25][CH:26]=2)[N:21]([CH3:41])[N:20]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:41][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=2[C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[C:34]([NH:39][CH3:40])[N:33]=[CH:32]3)[C:19]([NH:18][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)=[N:20]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1-bromo-3-(trifluoromethyl)benzene (19 μL, 138 μmol), tris(dibenzylideneacetone)dipalladium (0) (3.5 mg, 3.8 μmol), sodium t-butoxide (17 mg, 176 μmol), 6-(3-amino-1,6-dimethyl-1H-indazol-7-yl)-N-methylquinazolin-2-amine (40 mg, 126 μmol) and X-Phos (6.7 mg, 14 μmol) in toluene (3 mL) was purged with nitrogen and heated in a microwave reactor at 130° C. for 33 min. Solvent was removed in vacuo and the residue was purified by flash chromatography (25-50% EtOAc hexane) to give the title compound. MS (M+H)+ 463.

Workup

customwas purged with nitrogen
customSolvent was removed in vacuo
customthe residue was purified by flash chromatography (25-50% EtOAc hexane)

Sources & evidence

ORD record: ord-33607312e7f84f1099fff2d68597b35f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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