Diphenylmethylidenehydrazine → HCID 59799038, compound

HRID 1013099Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15](OS(C(F)(F)F)(=O)=O)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](=[N:41][NH2:42])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=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]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:42][N:41]=[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.39 g, 10.2 mmol) in dry, degassed toluene (100 mL) under nitrogen, then add benzophenone hydrazone (2.00 g, 10.2 mmol), sodium tert-butoxide (1.37 g, 14.3 mmol), BINAP (635 mg, 1.02 mmol) and bis(dibenzylideneacetone)palladium (0) (280 mg, 0.306 mmol). Stir at 100° C. for 8 hr, cool to RT, concentrate and purify (silica gel chromatography, eluting with 95:5 2-methylpentane:EtOAc) to give the title compound (4.2 g, 87%).

Workup

customin dry
customdegassed toluene (100 mL) under nitrogen
temperaturecool to RT
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 95:5 2-methylpentane:EtOAc)

Sources & evidence

ORD record: ord-001b6970d51940bda81ee4f9173a14ad
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981882B2

Reaction notes

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