Dimethylformamide → 5-Bromo-3-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine

HRID 908460Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][N:14]=3)[O:8][C:4]=2[CH:3]=1.CN(C=O)C.C1C(=O)N([Br:30])C(=O)C1>C(OCC)(=O)C>[Br:30][C:13]1[N:14]=[C:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([F:1])[CH:17]=[CH:16][C:5]=3[N:6]=2)[C:10]([NH2:15])=[N:11][CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

3-(6-Fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine (300 mg) was dissolved into DMF (15 ml) at 50° C. N-bromosuccimide (325 mg) was added. The mixture was stirred at 40° C. for 2 hours. The resulting mixture was diluted with ethyl acetate (15 ml), and washed with brine (10 ml×3). The organic layer was dried and concentrated to give 5-bromo-3-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-amine, which was used in the next reaction without further purification.

Workup

washwashed with brine (10 ml×3)
customThe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-cf2e7f42885d4959a29579096dabe208
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

Loading…