HCID 86731238, compound → HCID 86731237, compound

HRID 2277181Notes

Reaction equation

HRID 2277181 reaction equation
C(O[C:9]1[C:14]([F:15])=[C:13]([O:16]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[NH:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)=[C:28]([F:37])[CH:27]=1)C1C=CC=CC=1>[C].[Pd].C1COCC1>[CH:34]1([CH2:33][O:32][C:29]2[CH:30]=[CH:31][C:26]([C:25]3[O:38][C:9]4[C:14]([F:15])=[C:13]([OH:16])[CH:12]=[CH:11][C:10]=4[N:24]=3)=[CH:27][C:28]=2[F:37])[CH2:36][CH2:35]1

Participants

4

Reactant 1

HCID 86731238HCID 86731238, compound

Product 1

HCID 86731237HCID 86731237, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(2,4-bis(benzyloxy)-3-fluorophenyl)-4-(cyclopropylmethoxy)-3-fluorobenzamide (12.3 g), 10% palladium-carbon (containing water (50%), 12.0 g) and THF (80 mL) was stirred at room temperature for 20 min under a hydrogen atmosphere. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure, and the solid was washed with diethyl ether. To a solution of the obtained solid, hexachloroethane (14.6 g) and triphenylphosphine (16.2 g) in acetonitrile (50 mL) was added triethylamine (10.3 mL) at 0° C., and the mixture was stirred at room temperature for 15 min, and then with heating at 80° C. for 2 hr. The reaction mixture was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.96 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. washthe solid was washed with diethyl ether
  4. additionTo a solution of the obtained solid, hexachloroethane (14.6 g) and triphenylphosphine (16.2 g) in acetonitrile (50 mL) was added triethylamine (10.3 mL) at 0° C.
  5. stirringthe mixture was stirred at room temperature for 15 min
  6. temperaturewith heating at 80° C. for 2 hr
  7. filtrationThe reaction mixture was filtered
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-64086a7515b1403091d63d02935ddff1
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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