Sodium Bicarbonate → HCID 22676778, compound

HRID 1006287Notes

Reaction equation

HRID 1006287 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)(=[O:20])=[O:19])[C:10]=2[C:31]([O:33]C(C)(C)C)=[O:32])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)(=[O:19])=[O:20])[C:10]=2[C:31]([OH:33])=[O:32])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22676722HCID 22676722, compound

Product 1

HCID 22676778HCID 22676778, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]sulfonyl}indole-2-carboxylate (Example 27, 45 mg, 0.085 mmol) was dissolved in trifluoroacetic acid (0.4 mL). The resulting mixture was allowed to stir for 5 minutes. The reaction mixture was treated with a saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate (3×4 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 3-(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]sulfonyl}indole-2-carboxylic acid as an oil (17 mg, 42%): 1H (acetone-d6) δ 3.70 (s, 3 H), 6.85-6.89 (m, 2 H), 7.20-7.34 (m, 2 H), 7.47 (dd, J=0.6, 8.1 Hz, 1 H), 7.60-7.68 (m, 3 H), 7.83 (br d, 1 H), 8.06 (d, J=8.2 Hz, 1 H), 8.63 (m, 2 H); mass spectroscopy HPLC ES MS m/z (rel abundance) 476 ((M+H)+, 48%).

Workup

  1. extractionextracted with ethyl acetate (3×4 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0718e0f9c9674bbe8020f64e001e9030
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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