4-(3-Cyclopent-1-enyl-indole-1-sulfonyl)-benzoic acid methyl ester → HCID 58975006, compound

HRID 736988Notes

Reaction equation

HRID 736988 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[CH2:26][CH2:25][CH2:24][CH:23]=3)=[CH:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[CH:14]2)(=[O:11])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 589750154-(3-Cyclopent-1-enyl-indole-1-sulfonyl)-benzoic acid methyl ester

Product 1

HCID 58975006HCID 58975006, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4-(3-cyclopent-1-enyl-indole-1-sulfonyl)-benzoic acid methyl ester (2.2 g, 5.77 mmol) in ethanol (25 mL) and ethyl acetate (25 mL) and hydrogenate with 10% palladium on carbon (300 mg) at 33 psi for 16 h. Filter the catalyst over celite and back-wash with 1:1 ethanol/ethyl acetate (50 mL). Concentrate to give a dark solid and dissolve in 1:1 ethyl acetate/hexanes (50 mL) and pass through a silica gel plug. Back-wash the plug with 1:1 ethyl acetate/hexanes (100 mL) and concentrate the filtrate to an oil, which solidifies upon standing and found to be pure title compound (2.0 g, 90%); 1H NMR DMSO-d6) δ8.10 (m, 4H), 7.93 (d, J=8.2 Hz, 1H), 7.55 (d, J=7.7 Hz, 1H), 7.53 (s, 1H), 7.36 (t, J=7.1 Hz, 1H), 7.28 (t, J=7.7 Hz, 1H), 3.84 (s, 3H), 3.16 (m, 1H), 2.08 (m, 2H), 1.62 (m, 6H); MS (ESI) m/z 384 (m+H).

Workup

  1. filtrationFilter the catalyst over celite
  2. washback-wash with 1:1 ethanol/ethyl acetate (50 mL)
  3. concentrationConcentrate
  4. customto give a dark solid
  5. washBack-wash the plug with 1:1 ethyl acetate/hexanes (100 mL)
  6. concentrationconcentrate the filtrate to an oil, which

Sources & evidence

ORD record
ord-99be2490fb85423084ed58b34ceec1cd
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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