Dimethylformamide → 5-bromo-N,N-dimethyl-1H-indazol-3-amine

HRID 661037Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=C2N.IC.COC(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].[CH3:26][N:27]([CH:29]=O)[CH3:28]>O>[Br:1][C:2]1[CH:10]=[C:9]2[C:8](=[CH:4][CH:3]=1)[NH:7][N:6]=[C:29]2[N:27]([CH3:28])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 25 mL round-bottom flask, was added 5-bromo-1H-indazol-3-amine (2.0 g, 9432 μmol), 2.0 M iodomethane in tert-butyl methyl ether (587 μL, 9432 mmol), 1.5 g of Na2CO3, and 5 mL of DMF. The reaction mixture was heated to 80° C. for 6 hours. The reaction mixture was then diluted with 30 mL of water and extracted twice with 50 mL of EtOAc. The organic layers were combined, concentrated, and purified by a silica gel column chromatography separation on an ISOC instrument, eluting with 0-60% EtOAc in hexane to give 5-bromo-N,N-dimethyl-1H-indazol-3-amine (45 mg, 2.0% yield), MS m/z: 241 (M+1); and 5-bromo-N-methyl-1H-indazol-3-amine (550 mg, 26% yield), MS m/z: 227 (M+1).

Workup

extractionextracted twice with 50 mL of EtOAc
concentrationconcentrated
custompurified by a silica gel column chromatography separation on an ISOC instrument
washeluting with 0-60% EtOAc in hexane

Sources & evidence

ORD record: ord-1fe37e02c88e46d398a06cad02d3481b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084479B2

Reaction notes

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