Hydrogen Bromide → 5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole

HRID 2390428Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of NaNO2 (0.20 g, 2.8 mmol) in H2O (5 mL) was cooled in a wet ice bath and treated with a solution of 1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-amine (0.65 g, 2.8 mmol) in 48% aqueous HBr (2 mL). The resulting mixture was added to a pre-heated solution of CuBr (0.49 g, 3.4 mmol) in 48% aqueous HBr (2 mL) at 100° C. After stirring at 100° C. for 15 min, the dark mixture was allowed to cool. The solids were isolated by filtration, washed with 1N NaOH, and dried under vacuum. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 95:5 to 90:10 gave the title compound (0.21 g, 25%) as a brown solid: ESI MS m/z 294 [M+H]+.

Workup

temperatureto cool
customThe solids were isolated by filtration
washwashed with 1N NaOH
customdried under vacuum
customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 95:5 to 90:10

Sources & evidence

ORD record: ord-aba671fdee9e4728a765663fbd13dd0e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273770B2

Reaction notes

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