Hydrochloric Acid → 3-Bromo-1-(triphenylmethyl)-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid

HRID 588095Notes

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[N:4]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[OH-].[K+].Cl>CO>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]([C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of methyl 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylate (6.0 g, 12.04 mmol) in MeOH (60 mL) was added KOH (1 N, 42.1 mL, 42.1 mmol). The reaction mixture was heated to 50° C. for 1 h. After cooling down to room temperature, 1 N HCl was added until the pH of the reaction mixture reached 4. The solid was collected by filtration and washed with H2O to afford 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid. MS ESI calc'd. for C26H19BrN3O2 [M+H]+ 484. found 484.

Workup

temperatureAfter cooling down to room temperature
filtrationThe solid was collected by filtration
washwashed with H2O

Sources & evidence

ORD record: ord-74a8b6bd8352453d9ba1d70da6e44860
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

Loading…