Cesium carbonate → (S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate

HRID 1095670노트

반응식

HRID 1095670 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:16]3[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:20][C:15]3=[N:14][CH:13]=1)[CH:8]=[CH:7]2.[NH2:26][C@@H:27]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28]1.C([O-])([O-])=O.[Cs+].[Cs+].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.CC([O-])=O.CC([O-])=O.[Pd+2].ClCCl>[CH3:25][O:24][CH2:23][CH2:22][O:21][C:19]1[CH:18]=[CH:17][N:16]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:2]([NH:26][C@H:27]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28]5)[CH:3]=[CH:4][CH:5]=4)[N:10]=3)=[CH:13][N:14]=[C:15]2[CH:20]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 667815638-Bromo-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline

생성물 1

HCID 44185162(S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

A stream of argon was passed through a mixture of 8-bromo-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline (0.100 g, 0.2511 mmol), (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (0.05537 ml, 0.3264 mmol), Cs2CO3 (0.1145 g, 0.3515 mmol), Pd(OAc)2 (0.01127 g, 0.05022 mmol) and rac-BINAP (0.01564 g, 0.02511 mmol) in toluene (1 mL) for 15 minutes. The mixture was heated to 100° C. for 18 hours. The mixture was then allowed to cool to ambient temperature and dichloromethane was added. After stirring 30 minutes, the resulting mixture was filtered and the filtrate was concentrated to yield the title compound as an oil. MS APCI (+) m/z 504.1 (M+1) detected.

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationthe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-acfa1ff443ab40f290df50ff6e5d5270
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138181B2

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