Cesium carbonate → 1-[5-(2,6-dimethyl-phenyl)-1-(6-ethyl-2-methoxy-pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

HRID 472047노트

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HRID 472047 반응식
[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[N:13]=[C:12]([N:14]2[C:18]3=[CH:19][N:20]=[C:21]([C:23]4[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:30])[CH:22]=[C:17]3[C:16]([CH:31]([OH:37])[CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:15]2)[CH:11]=[C:10]([CH2:38][CH3:39])[N:9]=1>CO>[CH3:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[C:21]1[CH:22]=[C:17]2[C:16]([CH:31]([OH:37])[CH:32]([CH2:33][CH3:34])[CH2:35][CH3:36])=[CH:15][N:14]([C:12]3[CH:11]=[C:10]([CH2:38][CH3:39])[N:9]=[C:8]([O:4][CH3:1])[N:13]=3)[C:18]2=[CH:19][N:20]=1

참가 물질

4

반응물 2

HCID 10796Cesium carbonateHCID 866240821-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

생성물 1

HCID 582699311-[5-(2,6-dimethyl-phenyl)-1-(6-ethyl-2-methoxy-pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

Cs2CO3 (85 mg, 0.26 mmol) is added to a solution of 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol (100 mg, 0.22 mmol) in MeOH (4 mL). The mixture is heated at 60° C. for 30 min. The mixture is concentrated under reduced pressure, diluted with water (5 mL), and the product is extracted with DCM. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue silica gel (hexane-EtOAc, 1:1) gives 1-[5-(2,6-dimethyl-phenyl)-1-(6-ethyl-2-methoxy-pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol as colorless oil: 1H NMR (CDCl3) 10.18 (s, 1H), 8.39 (s, 1H), 7.54 (s, 1H), 7.27-7.12 (m, 3H), 6.41 (s, 1H), 5.00 (d, J=6 Hz, 1H), 4.12 (s, 3H), 2.78 (dd, J=7, 15 Hz, 2H), 2.075 (s, 6H), 1.39 (t, J=7 Hz), 2.05-1.26 (m, 5H), 0.92 (t, J=7 Hz, 6H); LCMS (1) m/z 459.33 (2.65 min).

후처리

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additiondiluted with water (5 mL)
  3. extractionthe product is extracted with DCM
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6a9f7ff1133e41839da6ea84e96d5d04
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633193B2

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