Methyl iodide → tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate

HRID 475307Notes

Reaction equation

HRID 475307 reaction equation
[C:1](=[N:14][CH2:15][C:16]1[C:17]([Cl:32])=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=[CH:19]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[CH3:35]C(C)([O-])C.[K+]>C1COCC1.CCOC(C)=O>[C:1](=[N:14][CH:15]([C:16]1[C:17]([Cl:32])=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH:20]=[CH:19]2)[CH3:35])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86694758tert-butyl 5-[(benzhydrylideneamino)methyl]-4-chloro-1H-indole-1-carboxylate

Product 1

HCID 86694759tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylateYield 94.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 322 (1.22 g, 2.74 mmol) and iodomethane (0.17 mL, 2.74 mmol) in anhydrous THF (22.3 mL) at 0° C. was added dropwise a solution of potassium tert-butoxide (358.4 mg, 3.098 mmol) dissolved in THF (˜0.50 mL) over 5 min. The reaction mixture was stirred at RT under N2 for 3 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 1.19 g (94.6%) of tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate (324) as a foam: MS (ESI) m/z=459.1 [M+1]+.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-defddda3bdd849a884dfd04136d9ccc2
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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