Hydrochloric Acid → 3-bromo-1-trityl-1H-indazole-5-carboxylic acid

HRID 1467318Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]CC)=[O:12])[CH:9]=2)[N:4]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[Li+].[OH-].Cl>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-bromo-1-trityl-1H-indazole-5-carboxylate (5.3 g, 20 mmol) in THF (80 mL), was added LiOH (30 mL, 1 N) and the reaction mixture was stirred at 50° C. for overnight. HCl (1 N) was added to adjust the pH˜4. Then ethyl acetated (100 mL) was added. The organic layer was separated and the aqueous layer was extract three times with ethyl acetate (20 mL each). The combined organic was washed with water (30 mL×3). Dry over Na2SO4 and concentrated on vacuum to give desired product as light yellow solid (4.8 g).

Workup

additionwas added
customThe organic layer was separated
extractionthe aqueous layer was extract three times with ethyl acetate (20 mL each)
washThe combined organic was washed with water (30 mL×3)
dry with materialDry over Na2SO4
concentrationconcentrated on vacuum

Sources & evidence

ORD record: ord-e2f426245ca04bb3b99a381e72ea3e00
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999957B2

Reaction notes

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