Diphenylmethylidenehydrazine → N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

HRID 2066918Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[C:12](=[N:25][NH2:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12](=[N:25][NH:26][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 5-bromoisoquinoline (200 mg, 0.96 mmol), benzhydrylidene-hydrazine (189 mg, 0.96 mmol), palladium diacetate (2.2 mg, 0.0096 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 6 mg, 0.0096 mmol) in dry toluene (1 mL), sodium tert-butoxide (130 mg, 1.34 mmol) was added and the mixture was heated at 85° C. for 4 hours. The mixture, cooled to room temperature, was filtered over celite and the pad was washed with diethylether. The solvent was evaporated under vacuum and the residue was purified by flash chromatography with hexane/ethylacetate 7/3 as eluant, affording 268 mg of the title compound (86% yield).

Workup

additionwas added
temperatureThe mixture, cooled to room temperature
filtrationwas filtered over celite
washthe pad was washed with diethylether
customThe solvent was evaporated under vacuum
customthe residue was purified by flash chromatography with hexane/ethylacetate 7/3 as eluant

Sources & evidence

ORD record: ord-28b008bb2b374d92a432d79f2420c568
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293762B2

Reaction notes

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