Dichloromethane → 1-[2-(2-cyclopent-1-enyl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 547480ノート

反応式

HRID 547480 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]3[C:16]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[C:23]1(B(O)O)[CH2:27][CH2:26][CH2:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:23]1([C:2]2[CH:7]=[C:6]([C:8]3[N:9]=[C:10]4[C:16]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][NH:14][C:11]4=[N:12][CH:13]=3)[CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:26][CH2:25][CH:24]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 578296311-[2-(2-chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

生成物 1

HCID 578295861-[2-(2-cyclopent-1-enyl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one収率 25%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 1-[2-(2-chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.060 g, 0.19 mmol), cyclopenten-1-yl boronic acid (0.032 g, 0.29 mmol), potassium carbonate (0.101 g, 0.73 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.012 g, 0.015 mmol) in 3 mL of 1,4-dioxane and 0.75 mL of water was stirred at 160° C. in a microwave for 30 min. The resulting black suspension was partitioned between 30 mL of ethyl acetate and 30 mL of water, and the aqueous layer was extracted with 30 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->60% EtOAc/hexanes) afforded 0.016 g (25%) of 1-[2-(2-cyclopent-1-enyl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a pale yellow solid.

後処理

  1. customThe resulting black suspension was partitioned between 30 mL of ethyl acetate and 30 mL of water
  2. extractionthe aqueous layer was extracted with 30 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-663e160ccd854e49aef29575c4dedcb9
出典データセット
uspto-grants-2011_05
特許番号
US07939531B2

反応ノート

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