N-bromobutanimide → HCID 178489113, compound

HRID 1628089Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[C:13]4[CH:20]=[CH:19][NH:18][C:14]4=[N:15][CH:16]=3)[N:11]([CH3:21])[N:10]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[Br:29][C:20]1[C:13]2[C:14](=[N:15][CH:16]=[C:17]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[N:10][N:11]([CH3:21])[C:12]3=2)[NH:18][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.264 g, 0.949 mmol; Example #AU.1.1) in DMF (3 mL) was added NBS (0.169 g, 0.949 mmol). The mixture was allowed to stir at about rt for about 16 h. Additional NBS (0.085 mg, 0.478 mmol) was added and the mixture was heated to about 50° C. for about 3 h. The mixture was purified by flash chromatography (40 g silica gel column, 10 to 100% EtOAc/heptane) to give 8-bromo-3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.150 g, 44%). LC/MS (Table 2, Method a) Rt=2.35 min.; MS m/z: 357 (M+H)+. Syk IC50=A.

Workup

customThe mixture was purified by flash chromatography (40 g silica gel column, 10 to 100% EtOAc/heptane)

Sources & evidence

ORD record: ord-3e0b0030690f433cb0e81a31f9cc7b40
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

Loading…