Sodium Bicarbonate → HCID 11329007, compound

HRID 916177Notes

Reaction equation

HRID 916177 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[F:25][C:26]([F:39])([F:38])[O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>ClCCl>[F:39][C:26]([F:25])([F:38])[O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=[C:9]3[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 69435288HCID 69435288, compound

Product 1

HCID 11329007HCID 11329007, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-aminophenyl)-1H-indole-2-carboxylic acid (0.4 g, 1.59 mmol) in 10 mL of 1:1 of dichloromethane/sat. aqueous sodium bicarbonate was added 4-trifluoromethoxy-benzenesulfonyl chloride (0.40 g, 1.53 mmol). After being stirred at room temperature for 1 hour the solid was collected and purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min) to afford 0.105 g (15%) of the title compound as a pale yellow solid: 1H NMR (DMSO-d6) δ 6.89(d, J=8.3 Hz, 1H), 7.10-7.30 (m, 6H), 7.39 (d, J=2.1 Hz, 1H), 7.60 (d, J=7.2 Hz, 2H), 7.71 (d, J=6.0 Hz, 1H), 7.90-8.00 (m, 2H), 10.63 (br s, 1H), 12.74 (br s, 1H); MS (ESI) m/z 477 (MH+); MS (ESI) m/z 475 ([M−H]−); HRMS calcd for C22H16F3N2O5S: 477.0721; found (ESI+): 477.0719; Anal. calcd for C22H15F3N2O5S.0.2H2O: C, 55.05; H, 3.23; N, 5.84. Found: C, 54.97; H, 3.41; N, 5.82.

Workup

  1. customwas collected
  2. custompurified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min)

Sources & evidence

ORD record
ord-85337e4654d84678a47fc5b00bff98d0
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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