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

HRID 79532노트

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HRID 79532 반응식
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

참가 물질

7

반응물 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)-

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9485091727a042dd83558ff672d029d0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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