Cesium carbonate → HCID 66556098, 화합물

HRID 1629938노트

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HRID 1629938 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.Cl[C:20]1[N:25]=[C:24]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)[CH:23]=[N:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.C(Cl)(Cl)Cl>[N:26]1([C:24]2[N:25]=[C:20]([C:9]3[CH:10]=[C:11]4[CH:17]=[CH:16][NH:15][C:12]4=[N:13][CH:14]=3)[CH:21]=[N:22][CH:23]=2)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 534081871-(6-Chloro-2-pyrazinyl)-2,3-dihydro-1H-indole

생성물 1

HCID 66556098HCID 66556098, 화합물

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

The starting material 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (124) (50 mg, 0.205 mmol, 1 eq) and 1-(6-chloropyrazin-2-yl)indoline (88) 423 mg, 0.185 mmol, 0.9 eq) in DME (7 mL) was degassed and purged under argon atmosphere for 10 min. To this reaction mixture was charged Cs2CO3 (133 mg, 0.410 mmol, 2 eq) followed by addition of Pd(dpp)Cl2 (6 mg, 0.00819 mmol, 0.04 eq) and degassing and purging under argon for additional minutes was performed. The reaction mixture was heated at 90° C. for 12 h in a sealed tube. After completion of the reaction, the reaction mixture was diluted with CHCl3 and filtered through Celite. The solvents were distilled off and the crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3 to obtain pale yellow solid compound 5-(6-(indolin-1-yl)pyrazin-2-yl)-1H-pyrrolo[2,3-b]pyridine 134 in 12 mg quantity. The compound 134 was confirmed by 1HNMR and LCMS. 1H NMR (400 MHz, CDCl3) δ: 9.06 (s, 2H), 8.59 (s, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.44 (m, 1H), 8.16 (s, 1H), 7.41 (m, 1H), 6.99 (m, 1H), 4.21 (m, J=8.53, 2H), 3.33 (m, J=341.82, 2H); MS m/z 313.9 (M+H)+.

후처리

  1. custompurged under argon atmosphere for 10 min
  2. customdegassing
  3. custompurging under argon for additional minutes
  4. customAfter completion of the reaction
  5. filtrationfiltered through Celite
  6. distillationThe solvents were distilled off
  7. customthe crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3

출처 및 근거

ORD 기록
ord-7840a2f383164126bea7a183fe28984f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791112B2

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