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

HRID 387258Notes

Reaction equation

HRID 387258 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]CC)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17]1.[OH-].[Na+]>O.CO>[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:16]1[CH2:20][CH2:19][S:18](=[O:21])(=[O:22])[CH2:17]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59332778Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylate

Product 1

HCID 593327155-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylate (0.596 g, 1.54 mmol) was dissolved in water (8.2 mL) and methanol (13.8 mL). A 6M NaOH solution (2.55 mL) was added and heated to 85° C. for 1.5 hours. The methanol was then concentrated and the solution was acidified with 6M HCl. The resulting white solid was filtered and dried to give 0.503 g (91%) of product.

Workup

  1. concentrationThe methanol was then concentrated
  2. filtrationThe resulting white solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-60ce3eee8c244324ba2dcf76012b0e48
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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