Sodium hydride → Methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate

HRID 860708Notes

Reaction equation

HRID 860708 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]=[CH2:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:31][C:32](=[CH2:37])[C:33]([O:35][CH3:36])=[O:34]>C1COCC1>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH2:31])[C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]=[CH2:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 58765232methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

Product 1

HCID 58765271Methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 3-cyclohexyl-2-(2-vinylphenyl)-1H-indole-6-carboxylate (7, R2=H) 508 mg, 1.4 mmol) was dissolved in THF (5 mL) under N2 and cooled to 0° C. Sodium hydride (143 mg, 60% suspension in mineral oil, 3.57 mmol) was added and the mixture was stirred at 0° C. for 5 min, when a solution of methyl 2-(bromomethyl)acrylate (276 mg, 1.54 mmol) in THF (1.5 mL) was added dropwise. Stirring was continued for 30 min at 22° C. The reaction was quenched with a saturated aqueous solution of ammonium chloride (20 mL) and extracted with EtOAc (2×30 mL) and CH2Cl2 (30 mL). The organic extracts were combined and dried over sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel using hexane/ethyl acetate (0–20%) to afford the title compound as a pale yellow solid (641 mg, 99%). ESI-MS m/z 458 (MH+).

Workup

  1. stirringStirring
  2. waitwas continued for 30 min at 22° C
  3. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride (20 mL)
  4. extractionextracted with EtOAc (2×30 mL) and CH2Cl2 (30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2337b15bed044708801a2995f2b94e49
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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