N-bromobutanimide → 6-Bromo-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridine

HRID 1374711Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([F:23])[CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:24][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([F:23])[CH:18]=2)[CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridine (Example 27. 937 mg, 3.05 mmol) in DMF (20 mL) was added N-bromosuccinimide (651 mg, 3.66 mmol). The reaction mixture was heated at 60° C. for about 5 h and then allowed to cool to room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with dichloromethane. The organic extracts were dried (MgSO4) and the solvents removed under vacuum. The residue was purified by silica gel chromatography to give the title compound. 0.604 g (50%). 1H NMR (CDCl3) δ 8.68 (s, 1H), 8.20 (d, 1H, J=5.4 Hz), 7.53 (m, 3H), 7.35 (dd, 1H, J=9.3, 1.2 Hz), 7.10 (m, 3H), 7.00 (s, 1H). MS (ES+ve) 387 (50, M+, M+3).

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with dichloromethane
dry with materialThe organic extracts were dried (MgSO4)
customthe solvents removed under vacuum
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-6af357b8fa6f4a7493d680bed1b0c2d4
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166597B2

Reaction notes

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