1,2-Dichloroethane → 3,4-Difluorobenzyl 1-Benzyl-6-(ethoxycarbonyl)-2-isopropyl-1H-indole-3-carboxylate

HRID 40075Notes

Reaction equation

HRID 40075 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=2)[C:10]([C:22]([OH:24])=[O:23])=[C:9]1[CH:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:36]O>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=2)[C:10]([C:22]([O:24][CH2:36][C:35]2[CH:38]=[CH:39][C:40]([F:41])=[C:33]([F:32])[CH:34]=2)=[O:23])=[C:9]1[CH:25]([CH3:26])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 5228333,4-Difluorobenzyl alcoholHCID 597623601-Benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic Acid2×

Product 1

HCID 597624113,4-Difluorobenzyl 1-Benzyl-6-(ethoxycarbonyl)-2-isopropyl-1H-indole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure E,1-benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic acid (Compound 39, 39 mg, 0.1 1 mmol) in CH2Cl2 (4 ml) was added EDC (35 mg, 0.22 mmol) and DMAP (16 mg, 0.15 mmol), followed by 3,4-difluorobenzyl alcohol (20 mg, 0.15 mmol). The reaction was stirred at room temperature for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as a yellow oil.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-bd5b4221ccbf4dd0bf0b3c680a198869
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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