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

HRID 40693ノート

反応式

HRID 40693 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-58171aae7fd94b37a68ecf7ba112ffeb
出典データセット
uspto-grants-2013_09
特許番号
US08530468B2

反応ノート

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