Triethylamine → 2-Ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindole

HRID 986226Notes

Reaction equation

HRID 986226 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:13]=2[CH:14]=1)=[O:5])[CH3:2].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[CH2:9][N:10]([C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24])[CH2:11][CH2:12][C:13]=2[CH:14]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 20158234HCID 20158234, compound

Product 1

HCID 201582272-Ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindoleYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-ethoxycarbonyl-4,5,6,7-tetrahydro-6-azaindole from Example 2 (8 g, 0.041 mole) in dichloromethane (200 ml) and triethylamine (4.15 g, 0.041 mole) was cooled to 0° C. and treated dropwise over 30 minutes with a solution of 2,2,2-trichloroethyl chloroformate (8.69 g, 0.041 mole) in dichloromethane (50 ml) and stirred subsequently for 30 minutes at room temperature. The mixture was quenched with water (50 ml), the organic layer separated, washed with water (50 ml), dried over sodium sulphate and evaporated to give a yellow oil which was chromatographed on silica gel (150 g) eluting with chloroform and chloroform:methanol (99:1) to give the expected pure product as a colourless solid (13.49 g, 89%), m.p. 126.5°-127° C. (from ether/hexane). Found: C, 42.24; H, 4.09; N, 7.54. C13H15Cl3N2O4 requires C, 42,24; H, 4.09; N, 7.58%.

Workup

  1. customThe mixture was quenched with water (50 ml)
  2. customthe organic layer separated
  3. washwashed with water (50 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give a yellow oil which
  7. customwas chromatographed on silica gel (150 g)
  8. washeluting with chloroform and chloroform:methanol (99:1)

Sources & evidence

ORD record
ord-38b26f746c2f45c98acb9f7f959a1d5a
Source dataset
uspto-grants-1987_12
Patent number
US04711882

Reaction notes

Loading…