Benzophenone imine → 1-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

HRID 1507605노트

반응식

HRID 1507605 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH3:16])([CH3:15])[C:9](=[O:14])[N:10]([CH:11]3[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[C:17]1([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[NH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.ClCCl.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH:11]1([N:10]2[C:4]3[CH:3]=[C:2]([N:24]=[C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:7]=[CH:6][C:5]=3[C:8]([CH3:16])([CH3:15])[C:9]2=[O:14])[CH2:13][CH2:12]1

참가 물질

8

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 900475066-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

생성물 1

HCID 900475681-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

시약·촉매·용매 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

To a suspension of 6-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (1.789 g, 7.56 mmol), diphenylmethanimine (2.05 g, 1.9 ml, 11.3 mmol, Eq: 1.5) and sodium tert-butoxide (1.23 g, 12.8 mmol) in toluene (48 ml) were added tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (156 mg, 151 mol) and BINAP (94.1 mg, 151 mol). The reaction mixture was heated to 100° C. for 18 hours and then diluted with dichloromethane. Silica gel was added and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel using heptane/EtOAc as eluent. The title compound was obtained as brown crystals (2.31 g).

후처리

  1. additionSilica gel was added
  2. customthe solvent was evaporated
  3. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-0a8c236c365f44ffa09cc015dfbee393
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221816B2

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