Iodine → HCID 178452208, compound

HRID 387580Notes

Reaction equation

[I:1]I.[C:3]1([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[C:11]3[CH:17]=[N:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOCC>[I:1][C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]=2[N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)[NH:15][N:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

I2 (0.421 g, 1.66 mmol) was added to a solution of tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.63 g, 0.830 mmol) and KOH (0.140 g, 2.49 mmol) (crushed by mortar and pestle) in DMF (10 mL). The resulting mixture was heated to 60° C. for 3 hours. Ether (20 mL) and saturated Na2SO3 (10 mL) were 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-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.40 g, 95%) as a solid. MS APCI (+) m/z 506.2 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.30 (s, 1H), 7.60 (m, 3H), 7.49 (m, 2H), 3.63 (m, 4H), 2.95 (m, 4H), 1.51 (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-2f801f359cd2482d82bfb0a37cbecd8f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372842B2

Reaction notes

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