Water → 5-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-indazole

HRID 879482Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[NH2:12].Cl.Cl[CH2:15][CH2:16][N:17]([CH2:19][CH2:20]Cl)[CH3:18].O.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[N:12]1[CH2:20][CH2:19][N:17]([CH3:18])[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

A vessel was charged with 5-bromo-1-methyl-1H-indazol-3-amine (250 mg, 1.10 mmol), 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (230 mg, 1.21 mmol), H2O (250 μL), K2CO3 (500 mg, 3.63 mmol), and DMF (2.5 mL). The vessel was sealed and heated to 100° C. for 18 h. The reaction was poured into EtOAc and washed with 5% w/v aq LiCl (3×), dried (Na2SO4), filtered, and concentrated. The residue was treated with DCM and purification by flash column chromatography on silica gel (hexanes/ethyl acetate to remove side products; then DCM/MeOH eluent to elute product) provided 5-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-indazole. LCMS-ESI+: calc'd for C13H17BrN4: 309.1, 311.1 (M+H+); Found: 309.2, 311.2 (M+H+).

Workup

customThe vessel was sealed
washwashed with 5% w/v aq LiCl (3×)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
additionThe residue was treated with DCM and purification by flash column chromatography on silica gel (hexanes/ethyl acetate
customto remove side products
washthen DCM/MeOH eluent to elute product)

Sources & evidence

ORD record: ord-38a56bff9d66423d94559736c6571690
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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