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

HRID 84109노트

반응식

HRID 84109 반응식
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH:6]([CH3:17])[CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1I)=[O:4].CC([O-])=O.[K+].[CH:25]1[CH:30]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:26]=1>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:30][C:25](=[CH2:26])[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH:6]1[CH3:17])=[O:4]

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 86590367N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine

생성물 1

HCID 22292791N-trifluoroacetyl-7-methoxy4-methyl-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine수율 430%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66ee94b390fd48e0bd17f4d77bdc2da8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846906B2

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