Triphenylphosphine → HCID 59850136, 화합물

HRID 2064183

반응식

HRID 2064183 반응식
Br[C:2]1[C:3]([F:24])=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:7]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:26]=1>C1(C)C=CC=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]>[CH:25]([C:2]1[C:3]([F:24])=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:7]=1)=[CH2:26]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 59850147N-(5-Bromo-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

생성물 1

HCID 59850136HCID 59850136, 화합물수율 314.8%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 1140Toluene용매

반응 조건

온도
130 °C

실험 절차

A solution of N-(5-bromo-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D78, 800 mg, ˜75% purity) and n-tributylvinyltin (0.697 ml, 2.3 mmol) in toluene (30 ml) was treated, under a positive flow of argon, with triphenylphosphine (129.8 mg, 0.5 mmol) and bis(dibenzylideneacetone)palladium(0) (170.1 mg, 0.297 mmol), then stirred and heated under argon atmosphere at 130° C. for 1.5 h. The mixture was filtered through a celite pad. The organic layer was washed with NH4OH (10% aq) and water, then dried over MgSO4 and concentrated. The mixture was purified on silica column (100 g of silica, methanol/dichloromethane, 5% to 20%, 15CV) to afford 550 mg of title compound.

후처리

  1. filtrationThe mixture was filtered through a celite pad
  2. washThe organic layer was washed with NH4OH (10% aq) and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe mixture was purified on silica column (100 g of silica, methanol/dichloromethane, 5% to 20%, 15CV)

출처 및 근거

ORD 기록
ord-cd3d7f9b8fec466bb48faa051fdb128f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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