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Sodium Hydroxide → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

HRID 387251
Notes
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Reaction equation

HRID 387251 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([O:15]C)=[O:14])[CH:12]=1)[N:9](C(OC(C)(C)C)=O)[CH:8]=[C:7]2[CH:24]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]1.BrC1C=C2C(=C(C(OCC)=O)C=1)N(C(OC(C)(C)C)=O)C=C2C1CCS(=O)(=O)CC1>CO.O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([OH:15])=[O:14])[CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:24]1[CH2:25][CH2:26][S:27](=[O:30])(=[O:31])[CH2:28][CH2:29]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 593326221-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylateHCID 593326271-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate

Product 1

HCID 593327515-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 6 M NaOH (12 mL, 72.0 mmol) was added to a suspension of 1-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (0.93 g, 1.912 mmol) and 1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (3.08 g, 6.16 mmol) in MeOH (50 mL) and water (25 mL) in a 250 mL round bottomed flask fitted with a reflux condenser. The reaction was heated at 85° C. (bath temp) for 1.5 h. The MeOH was removed by rotovap, and a solution of 6 M HCl was added until the mixture had attained a pH of ˜1 by pH paper. The yellow solid was filtered off, and the filtrate was extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure, and the residue was combined with the precipitate from the filtration and dried under house vacuum at 45° C. overnight. Recovered 2.98 g (86%) of the title compound.

Workup

  1. customfitted with a reflux condenser
  2. customThe MeOH was removed by rotovap
  3. additiona solution of 6 M HCl was added until the mixture
  4. filtrationThe yellow solid was filtered off
  5. extractionthe filtrate was extracted with EtOAc (3×10 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. filtrationthe residue was combined with the precipitate from the filtration
  9. customdried under house vacuum at 45° C. overnight
  10. customRecovered 2.98 g (86%) of the title compound

Sources & evidence

ORD record
ord-9f88d72c49364e71be998890b8bb3160
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372875B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes