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 547480노트

반응식

HRID 547480 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-663e160ccd854e49aef29575c4dedcb9
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939531B2

반응 노트

불러오는 중…