Dichloromethane → HCID 67345197, compound

HRID 1677425Notes

Reaction equation

HRID 1677425 reaction equation
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.CO[C:19]1[CH:20]=[C:21]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[CH:22]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.[C:39](=O)([O-])[O-:40].[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>[CH3:39][O:40][C:21]1([N:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)[CH:20]=[CH:19][CH:24]=[C:23]([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)[CH2:22]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneHCID 59541021HCID 59541021, compound

Product 1

HCID 67345197HCID 67345197, compoundYield 24%

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-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (55 mg, 0.2 mmol), 1-[3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine (67 mg, 0.22 mmol), potassium carbonate (70 mg, 0.51 mmol), Pd(dppf)Cl2.CH2Cl2 (12 mg, 0.015 mmol), 1.5 mL dioxane and 0.3 mL water was stirred at 160° C. in a microwave for 30 min. The resulting mixture was partitioned between ethyl acetate and water. The combined organic layers were dried over Na2SO4 and concentrated to give a dark brown residue. The crude product was purified by preparative thin layer chromatography using 140:9.5:0.5 CH2Cl2:MeOH:conc NH4OH as eluant. The resultant brown solid was washed with ethyl ether to provide 18 mg (24%) of 1-[2-(3-methoxy-3-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid. MP 245-256° C., M+H 379.

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate and water
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give a dark brown residue
  5. customThe crude product was purified by preparative thin layer chromatography
  6. washThe resultant brown solid was washed with ethyl ether

Sources & evidence

ORD record
ord-0b352ef859084e329719749d08907a66
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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