Iodine → HCID 178452246, compound

HRID 387569Notes

Reaction equation

[I:1]I.[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][C:11]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[C:6]2[CH:5]=[N:4]1.[OH-].[K+].[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOCC>[I:1][C:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[NH:3][N:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

I2 (0.920 g, 3.63 mmol) was added to tert-butyl 4-(1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.55 g, 1.81 mmol) and KOH (0.305 g, 5.44 mmol) (crushed by motar and pestle) in DMF (10 mL). The resulting mixture was warmed to 60° C. and stirred for 2 hours. Ether (20 mL) and saturated Na2SO3 (10 mL) were then added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.45 g, 58%) as a solid. MS APCI (+) m/z 430.0 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.31 (d, J=5.2 Hz, 1H), 6.63 (d, J=5.6 Hz, 1H), 3.63 (m, 4H), 3.18 (m, 4H), 1.44 (s, 9H).

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
customAfter removal of the solvent
customthe resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record: ord-175da6c8710b4f78853a05e5a7abb433
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372842B2

Reaction notes

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