Benzophenone imine → tert-butyl 5-[(benzhydrylideneamino)methyl]-4-chloro-1H-indole-1-carboxylate

HRID 475306Notes

Reaction equation

HRID 475306 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([Cl:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6]2.[C:20](=N)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.CCOC(C)=O>[C:20](=[N:1][CH2:2][C:3]1[C:4]([Cl:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH:7]=[CH:6]2)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 136809Benzophenone imineHCID 71272344tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylate

Product 1

HCID 86694758tert-butyl 5-[(benzhydrylideneamino)methyl]-4-chloro-1H-indole-1-carboxylateYield 67.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylate (1.147 g, 4.087 mmol) and benzophenone imine (0.75 mL, 4.496 mmol) in anhydrous DCM (39.3 mL) was stirred at 40° C. under N2 for 4 d. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with and EtOAc/heptane gradient (0 to 70% EtOAc) to afford 1.22 g (67%) of tert-butyl 5-[(benzhydrylideneamino)methyl]-4-chloro-1H-indole-1-carboxylate (322) as an oil: 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.5 Hz, 1H), 7.82-7.77 (m, 1H), 7.69 (d, J=7.2 Hz, 2H), 7.60-7.56 (m, 1H), 7.48 (d, J=8.2 Hz, 1H), 7.43 (d, J=8.9 Hz, 2H), 7.37 (d, J=7.0 Hz, 1H), 7.33 (t, J=7.3 Hz, 2H), 7.25-7.20 (m, 2H), 6.66 (d, J=3.7 Hz, 1H), 4.75 (s, 2H), 1.66 (s, 9H); MS (ESI) m/z=445.2 [M+1]+.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with and EtOAc/heptane gradient (0 to 70% EtOAc)

Sources & evidence

ORD record
ord-c4ef0a81c358417a8b31f4a52512587e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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