Sodium Carbonate → 2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 510168Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:11]([S:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])=[O:15])([CH3:13])[CH3:12].O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>O>[CH:11]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:19][CH:18]=1)(=[O:15])=[O:16])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

2-bromo-5H-pyrrolo[2,3-b]pyrazine (6.5 g, 32.82 mmol), (4-isopropylsulfonylphenyl) boronic acid (7.859 g, 34.46 mmol) and palladium triphenylphosphane complex (1.896 g, 1.641 mmol) were combined in a round bottomed flask. To this mixture was added dioxane (97.50 mL) and then an aqueous solution of Na2CO3 (49.23 mL of 2 M, 98.46 mmol). The resulting suspension was stirred at 100° C. overnight, then heating was stopped and water added. The resultant precipitate was collected and dried in vacuo at 40° C., to give the sub-title compound as a brown solid (9.45 g, 95% yield). 1H NMR (400.0 MHz, DMSO) δ 12.25 (s, 1H), 9.00 (s, 1H), 8.43 (d, J=8.4 Hz, 2H), 7.99-7.96 (m, 3H), 6.74 (d, J=3.5 Hz, 1H), 3.57 (s, 1H) and 1.20 (d, J=6.8 Hz, 6H) ppm; MS (ES+) 435.2.

Workup

temperatureheating
customThe resultant precipitate was collected
customdried in vacuo at 40° C.

Sources & evidence

ORD record: ord-444df652d22e40caa17383cec0aca44f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096602B2

Reaction notes

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