Cesium carbonate → Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79532ノート

反応式

HRID 79532 の反応式
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[CH:6][N:5]=[C:4]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:3]=12.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([N:31]3[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]3)=[C:3]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:4]3=[N:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 687603871H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-

生成物 1

HCID 68761257Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate収率 29.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

4-Chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (0.400 g, 1.00 mmol), tert-butyl piperazine-1-carboxylate (0.280 g, 1.50 mmol), Pd(OAc)2 (0.0225 g, 0.100 mmol), Xantphos (0.0870 g, 0.150 mmol), and Cs2CO3 (0.490 g, 1.50 mmol) were placed in degassed toluene (4 mL). The mixture was heated to 100° C. for 24 hours. The reaction was cooled to room temperature, filtered through celite, and concentrated. The product was purified (500:5 to 500:7 DCM:MeOH) to yield tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.160 g, 29.0% yield).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe product was purified (500:5 to 500:7 DCM:MeOH)

出典と根拠

ORDレコード
ord-9485091727a042dd83558ff672d029d0
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

読み込み中…