Methanol → 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylic acid

HRID 656014Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH:6]=[C:5]2[CH:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[CH2:23]1.[Li+].[OH-].CO>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:22]1[CH2:26][CH2:25][S:24](=[O:27])(=[O:28])[CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a microwave vial was added 1-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-1,7-dicarboxylate (432 mg, 0.91 mmol), LiOH (109 mg, 4.5 mmol), MeOH (6 mL) and H2O (3 mL). The mixture was heated to 80° C. for 30 min in the microwave. The reaction mixture was then purified via Gilson HPLC (TFA buffer) to give 99 mg of the title compound.

Workup

customThe reaction mixture was then purified via Gilson HPLC (TFA buffer)

Sources & evidence

ORD record: ord-3ace81f4c68841d39377ccee327b8322
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071584B2

Reaction notes

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