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Triphenylphosphine → N-trifluoroacetyl-7-methoxy4-methyl-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1010775
Notes
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Reaction equation

HRID 1010775 reaction equation
[CH2:1]([N:4]([CH:11]([CH3:22])[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1I)[C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])[CH:2]=[CH2:3].CC([O-])=O.[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[F:7][C:6]([F:9])([F:8])[C:5]([N:4]1[CH2:1][C:2](=[CH2:3])[C:14]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=2[CH2:12][CH:11]1[CH3:22])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 86611333HCID 86611333, compound

Product 1

HCID 22292791N-trifluoroacetyl-7-methoxy4-methyl-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepineYield 43%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium Bromide
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 6228DimethylformamideSolvent

Procedure

A solution of N-allyl,N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine (4.45 g, 10.8 mmol) in dimethylformamide (120 mL) was treated with KOAc (3.17 g, 32.3 mmol), n-Bu4NBr (3.47 g, 10.8 mmol), PPh3 (0.283 g, 1.08 mmol), Pd(OAc)2 (0.242 g, 1.08 mmol) and stirred overnight at 80 C. The product mixture was cooled to 20 C, filtered, diluted with water (200 mL), extracted with ether (3×200 mL), the combined organic phases washed with water (100 mL), brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 1.39 g of a yellow oil.

Workup

  1. temperatureThe product mixture was cooled to 20 C
  2. filtrationfiltered
  3. additiondiluted with water (200 mL)
  4. extractionextracted with ether (3×200 mL)
  5. washthe combined organic phases washed with water (100 mL), brine (100 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a79bb527fa684ed987cbfefb9b44cfa3
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977329B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes