Potassium Carbonate → HCID 178461050, compound

HRID 1943884Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18](=[O:40])[C:19]3[C:24]([F:25])=[CH:23][CH:22]=[C:21]([N:26](S(CCC)(=O)=O)[S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[C:20]=3[F:39])[CH:15]=2)[N:10](S(C2C=CC(C)=CC=2)(=O)=O)[N:9]=1>CO.O>[Br:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18](=[O:40])[C:19]3[C:24]([F:25])=[CH:23][CH:22]=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[C:20]=3[F:39])[CH:15]=2)[NH:10][N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

K2CO3 (0.151 g, 1.09 mmol) was added to a solution of N-(3-bromo-1-tosyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide (0.100 g, 0.136 mmol) in MeOH/H2O (4:1, 10 mL), and the reaction mixture was heated to 60° C. for 1 hour. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was taken up in ethyl acetate (100 mL) and washed with water (50 mL). The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1), hexanes/ethyl acetate (1:1) to give N-(3-bromo-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.024 g, 37%, 2 steps) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.7 (s, 1H), 8.5 (s, 1H), 7.7 (m, 1H), 7.1 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=472.2, 474.2.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
washwashed with water (50 mL)
customThe crude product was purified by column chromatography
washeluting with hexanes/ethyl acetate (2:1), hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-090cf6f899b94e48a5cc888fde151ebb
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394795B2

Reaction notes

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