N-bromobutanimide → 3-Bromo-5-cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

HRID 63533Notes

Reaction equation

[CH:1]1([C:4]2[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]3[C:6](=[CH:7][N:8]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Br:23]N1C(=O)CCC1=O>CN(C=O)C>[Br:23][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[N:9]=[C:10]2[C:6]=1[CH:5]=[C:4]([CH:1]1[CH2:3][CH2:2]1)[C:12]([N+:13]([O-:15])=[O:14])=[CH:11]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (ii) (1.08 g, 3.67 mmol) in DMF (15 mL) was added N-bromosuccinimide (780 mg, 4.40 mmol) and the resulting mixture stirred at 80° C. for 1.5 h. The reaction mixture was then cooled to RT and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was dried (MgSO4) and the volatiles removed in vacuo to give (iii) (1.37 g, >99%). ESI-MS: calculated [M+H]+ 373.01375.0. observed [M+H]+ 373.1/375.1.

Workup

temperatureThe reaction mixture was then cooled to RT
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in EtOAc (100 mL)
washwashed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL)
dry with materialThe organic phase was dried (MgSO4)
customthe volatiles removed in vacuo

Sources & evidence

ORD record: ord-e65bb998b6db4aa2915061dc575f6af6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447080B2

Reaction notes

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