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

HRID 547465노트

반응식

HRID 547465 반응식
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl:17][C:18]1[CH:23]=[C:22](B(O)O)[CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>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].O.O1CCOCC1>[Cl:17][C:18]1[CH:23]=[C:22]([C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:21]=[CH:20][N:19]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

생성물 1

HCID 578296311-[2-(2-chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one수율 32.2%

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-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (0.430 g, 1.53 mmol), 2-chloropyridine-4-boronic acid (0.362 g, 2.30 mmol), potassium carbonate (0.782 g, 5.66 mmol), Pd(dppf)Cl2.CH2Cl2 (0.098 g, 0.12 mmol), 10 mL dioxane and 2.5 mL water was stirred at 160° C. in a microwave for 30 min. The resulting red mixture was partitioned between 80 mL of ethyl acetate and 150 mL of water. The aqueous layer was extracted with two 80 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Silica gel chromatography (0->100% EtOAc/hexanes) afforded 0.155 g (32%) of 1-[2-(2-chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a red solid.

후처리

  1. customThe resulting red mixture was partitioned between 80 mL of ethyl acetate and 150 mL of water
  2. extractionThe aqueous layer was extracted with two 80 mL portions 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-feb5d30db265411ca606a4ad99d353a5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939531B2

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