Potassium Carbonate → 4-[5-amino-6-(1-ethyl-1-H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-yl]-N,N-dimethylbenzenesulfonamide

HRID 1817158Notes

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.[CH3:20][N:21]([CH3:34])[S:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])=[O:23].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>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:28]2[CH:27]=[CH:26][C:25]([S:22]([N:21]([CH3:34])[CH3:20])(=[O:23])=[O:24])=[CH:30][CH:29]=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

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), 4-dimethylaminosulphonylphenylboronic acid (0.046 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 HPLC to give 0.0079 g of the title compound.

Workup

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

Sources & evidence

ORD record: ord-c60ce536c5fb4ccba7d13c41de052ced
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598251B2

Reaction notes

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