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

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%.

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)

ORD record

ord-38b26f746c2f45c98acb9f7f959a1d5a

Source dataset

uspto-grants-1987_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04711882