Cesium carbonate → 5-(1H-pyrrolo[2,3-c]pyridin-5-ylamino)pyrazine-2-carbonitrile

HRID 40693노트

반응식

HRID 40693 반응식
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8](C(OC(C)(C)C)=O)[C:5]2=[CH:6][N:7]=1.[NH2:18][C:19]1[N:20]=[CH:21][C:22]([C:25]#[N:26])=[N:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCOCC1>[NH:8]1[C:5]2=[CH:6][N:7]=[C:2]([NH:18][C:19]3[N:20]=[CH:21][C:22]([C:25]#[N:26])=[N:23][CH:24]=3)[CH:3]=[C:4]2[CH:10]=[CH:9]1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 139252945-Aminopyrazine-2-carbonitrileHCID 59636374tert-butyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

생성물 1

HCID 442046495-(1H-pyrrolo[2,3-c]pyridin-5-ylamino)pyrazine-2-carbonitrile수율 45.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

A mixture of tert-butyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.030 g, 0.119 mmol), 5-aminopyrazine-2-carbonitrile (0.017 g, 0.142 mmol), cesium carbonate (0.077 g, 0.237 mmol), Xantphos (0.011 g, 0.019 mmol) and tris(benzylideneacetone)dipalladium (0) (0.009 g, 0.010 mmol) in dioxane (0.8 mL) was degassed by bubbling argon through the mixture for 10 minutes. The sealed reaction vessel was heated to 150° C. for 1 hour in a microwave reactor. The crude mixture was filtered through an SCX-2 acidic resin cartridge, eluting with 2 M ammonia in methanol. The basic filtrate was concentrated and purified by column chromatography to give the title compound (0.018 g, 0.054 mmol, 45%). LC-MS (3) Rt=1.30 min; m/z (ESI+) 237 (M+H).

후처리

  1. customwas degassed
  2. customby bubbling argon through the mixture for 10 minutes
  3. customThe sealed reaction vessel
  4. filtrationThe crude mixture was filtered through an SCX-2 acidic resin cartridge
  5. washeluting with 2 M ammonia in methanol
  6. concentrationThe basic filtrate was concentrated
  7. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-58171aae7fd94b37a68ecf7ba112ffeb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530468B2

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