Cyclopentene → HCID 22676838, compound

HRID 1006255Notes

Reaction equation

HRID 1006255 reaction equation
[CH:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1.C([O-])(=O)C.[K+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27](OS(C(F)(F)F)(=O)=O)[CH:28]=3)[N:23]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=3)[C:22]=2[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([CH:1]4[CH2:5][CH2:4][CH:3]=[CH:2]4)[CH:28]=3)[N:23]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=3)[C:22]=2[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

8

Reactant 3

HCID 8882CyclopenteneHCID 517044Potassium AcetateHCID 22676791HCID 22676791, compound

Product 1

HCID 22676838HCID 22676838, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyclopentene (0.44 mL, 341 mg, 5.0 mmol), palladium acetate (22 mg, 0.10 mmol), tetrabutylammonium bromide (322 mg, 1.0 mmol) and potassium acetate (295 mg, 1.0 mmol) were added to a stirred solution of ethyl 3-(4-tert-butylphenyl)-1-(3-methoxybenzyl)-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-indole-2-carboxylate (Example 125, 570 mg, 1.0 mmol) in N,N-dimethylformamide (5 mL). The reaction was stirred for 48 h and then diluted with ethyl acetate (100 mL). The solution was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 6:1 ethyl acetate/hexane gave 230 mg, (45%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.49-7.56 (m, 3 H), 7.37-7.43 (m, 3 H), 7.17-7.23 (m, 2 H), 6.68-6.92 (m, 3 H), 4.09 (q, 3 H), 3.92-4.01 (m, 1 H), 3.75 (s, 3 H), 2.31-2.50 (m, 3 H), 1.62-1.77 (m, 1 H), 1.39 (s, 9 H), 0.98 (t, 3 H).

Workup

  1. washThe solution was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-beb3c39e352b4fbb9fd71146daa41474
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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