Potassium Carbonate → HCID 68863391, compound

HRID 1817167Notes

Reaction equation

HRID 1817167 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([O:24][C:25]([N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1B(O)O)=[O:26])(C)(C)C.C([O-])([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>[CH:25]([OH:26])=[O:24].[CH2:18]([N:10]1[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]=[C:9]1[C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:28]2[NH:27][CH:31]=[CH:30][CH:29]=2)[N:3]=1)[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Product 1

HCID 68863391HCID 68863391, compoundYield 12.2%

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 (0.020 g, 0.063 mmol) (made in example 2), 1-(tert-butoxycarbonyl)pyrrole-2-boronic acid (0.052 g, 0.25 mmol), Pd(PPh3)2Cl2 (0.004 g, 0.0057 mmol) and K2CO3 (0.050 g, 0.25 mmol) were combined in 0.5 mL of N,N-dimethylformamide and heated to 200° C. in the SmithSynthesizer microwave for 8 minutes. The reaction mixture was concentrated in vacuo and the residue purified by HPLC to give 0.0027 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-4b16c692d7fe4aabbf0110eb45fed2f2
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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