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

HRID 1507605ノート

反応式

HRID 1507605 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 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)触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0a8c236c365f44ffa09cc015dfbee393
出典データセット
uspto-grants-2015_12
特許番号
US09221816B2

反応ノート

読み込み中…