Diphenylmethylidenehydrazine → HCID 86653535, compound

HRID 871705Notes

Reaction equation

HRID 871705 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:9](=[N:22][NH2:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:10]1([C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:22][NH:23][C:2]2[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 79304DiphenylmethylidenehydrazineHCID 5995285-Bromo-2-hydroxypyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxide

Product 1

HCID 86653535HCID 86653535, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2(1H)-pyridone (2.0 g, 11.5 mmol) in 25 mL dry toluene was treated with benzophenone hydrazone (2.50 g, 12.7 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (200 mg, 0.345 mmol), and sodium tert-butoxide (2.2 g, 23 mmol). The mixture was degassed with argon for 15 minutes. Added Pd(II)(OAc)2 (80 mg, 0.345 mmol) and stirred at 90° C. for 16 hours. Extracted using EtOAc/H2O (3×150 mL EtOAc, 1×150 mL brine). Dried using Na2SO4 and then purified by flash chromatography (silica, 0-12% MeOH/DCM) to afford 5-(2-(diphenylmethylene)hydrazinyl)pyridin-2(1H)-one (950 mg, 3.28 mmol, 29%). 1H NMR (300 MHz, DMSO-d6) δ 11.12 (s, 1H), 8.49 (s, 1H), 7.61-7.25 (m, 12H), 6.31 (d, 1H); LC-MS (ESI) m/z 290 (M+H)+.

Workup

  1. customThe mixture was degassed with argon for 15 minutes
  2. extractionExtracted
  3. customDried
  4. custompurified by flash chromatography (silica, 0-12% MeOH/DCM)

Sources & evidence

ORD record
ord-457d2f7d029744509d2d39de4e2c4898
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

Loading…