Potassium Carbonate → HCID 68862024, compound

HRID 1817168Notes

Reaction equation

HRID 1817168 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.B([C:23]1[N:24]([C:32]([O:34]C(C)(C)C)=[O:33])[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)(O)O.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:32]([OH:34])=[O:33].[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:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:3]=1)[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Product 1

HCID 68862024HCID 68862024, compoundYield 31.6%

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), tert-butyl 2-borono-1H-indole-1-carboxylate (0.062 g, 0.25 mmol), Pd(PPh3)2Cl2 (0.004 g, 0.0056 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 0.008 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-44484034b15d46ad95c3fc3681b2ee98
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

Loading…