Acetate → HCID 59852405, compound

HRID 2373177Notes

Reaction equation

HRID 2373177 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[N:10]([CH2:18][CH3:19])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:20]([O-:23])(=[O:22])[CH3:21].[C:24]([O-:27])([O-])=O.[K+].[K+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:11]2[CH:16]=[CH:15][C:24]([O:27][CH2:21][C:20]([OH:23])=[O:22])=[CH:13][CH:12]=2)=[N:3][C:4]=1[C:9]1[N:10]([CH2:18][CH3:19])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]=1

Participants

6

Reactant 3

HCID 175AcetateHCID 11430Potassium CarbonateHCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Product 1

HCID 59852405HCID 59852405, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

5-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.032 g, 0.10 mmol) (made in example 2), tert-butyl[4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)phenoxy]acetate (0.067 g, 0.20 mmol), Pd(PPh3)2Cl2 (0.0035 g, 0.005 mmol) and K2CO3 (0.050 g, 0.36 mmol) were combined in 0.5 mL of N,N-dimethylformamide and heated to 200° C. in the SmithSynthesizer microwave for 8 minutes and then for a further 8 minutes at 250° C. The reaction mixture was concentrated in vacuo and the residue purified by mass directed HPLC to give 0.0038 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by mass

Sources & evidence

ORD record
ord-7a6ca17ad49543999a83d0b81726db80
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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