Methanol → HCID 59332558, compound

HRID 656035Notes

Reaction equation

HRID 656035 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[CH2:21][CH:20]([CH3:22])[S:19](=[O:24])(=[O:23])[CH:18]([CH3:25])[CH2:17]1.CO.[OH-].[Na+]>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:16]1[CH2:17][CH:18]([CH3:25])[S:19](=[O:23])(=[O:24])[CH:20]([CH3:22])[CH2:21]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59332637HCID 59332637, compound

Product 1

HCID 59332558HCID 59332558, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 5-bromo-3-(2,6-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate (0.189 g, 0.441 mmol), was stirred in a methanol (5 mL)/water (3 mL) solution. 6M NaOH (0.735 mL, 4.41 mol, 10 eq) was added and the reaction was heated to 85° C. for 1.5 hours. LCMS analysis indicated the reaction was completed. The methanol was concentrated and the aqueous solution was acidified with 6M HCl. The resulting white solid was filtered and dried under vacuum to give 0.187 g (92%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-465cd33775254100bd2fd3ac1a4769dd
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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