Methanol → 3-(2-Hydroxypropan-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylic acid

HRID 1047639Notes

Reaction equation

[OH:1][C:2]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16]C)=[O:15])=[CH:11][CH:12]=2)[N:7]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[N:6]=1)([CH3:4])[CH3:3].CO.[OH-].[Na+]>O1CCCC1>[OH:1][C:2]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[N:7]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[N:6]=1)([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 3-(2-hydroxypropan-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylate (909.8 mg, 2.88 mmol) was dissolved in tetrahydrofuran (17.25 mL) and methanol (11.50 mL) at 25° C. 1M sodium hydroxide (11.50 mL, 11.50 mmol) was added and the reaction mixture heated to 50° C. The reaction mixture was allowed to stir for 15 min. The reaction was stopped, cooled to room temperature, quenched by addition of concentrated hydrochloric acid (0.950 mL), and concentrated under reduced pressure. The title compound (804.8 mg, 2.66 mmol, 93% yield) was recovered as a light orange/white solid. LC-MS: [M+1]=303.2.

Workup

customat 25° C
temperaturecooled to room temperature
customquenched by addition of concentrated hydrochloric acid (0.950 mL)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b7f5516a909343a783c7a5d6fd74e1e5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569512B2

Reaction notes

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