Sodium Hydroxide → [2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid

HRID 453613Notes

Reaction equation

HRID 453613 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:9]=[C:8]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[NH:18]3)=[CH:14][CH:13]=2)=[O:11])[S:7][C:6]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+]>CO.C1COCC1>[C:27]1([C:6]2[S:7][C:8]([C:10]([C:12]3[CH:20]=[C:19]4[C:15]([CH:16]=[C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[NH:18]4)=[CH:14][CH:13]=3)=[O:11])=[CH:9][C:5]=2[CH2:4][C:3]([OH:33])=[O:2])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86646414[2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid methyl ester

Product 1

HCID 25221754[2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.44 g (0.97 mmol) of 23 in 7 mL of MeOH and 7 mL of THF was added 1.5 mL (1.5 mmol) of 1 N NaOH solution. The resulting solution was stirred at room temperature for 4 h. The solvent was removed in vacuo, and the residue was diluted with 10 mL of H2O, acidified to pH˜3 with 1N HCl, and extracted with 30 mL of EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:1) to afford 0.36 g (87%) of 8: mp 238-240° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.5 (brs, 1H), 12.04 (s, 1H), 8.00 (s, 1H), 7.93 (d, J=7.4 Hz, 2H), 7.80 (s, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.59-7.48 (m, 9H), 7.38 (t, J=7.1 Hz, 1H), 7.07 (d, J=1.2 Hz, 1H), 3.69 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 186.6, 172.0, 147.4, 141.6, 141.0, 136.3, 132.6, 132.2, 131.9, 131.4, 130.4, 129.2, 129.1, 128.8, 128.3, 125.6, 125.4, 120.5, 99.3, 34.1; IR (KBr) cm−1 3417, 3054, 1713, 1596.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with 10 mL of H2O
  3. extractionextracted with 30 mL of EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/Hex 1:1)

Sources & evidence

ORD record
ord-4ccc19b4f4b84f3684631d8c2bdec399
Source dataset
uspto-grants-2013_07
Patent number
US08492428B2

Reaction notes

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