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 547480Notes

Reaction equation

HRID 547480 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-663e160ccd854e49aef29575c4dedcb9
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

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