Trifluoroacetic acid → 11-Cyclohexyl-10-oxo-7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole-3-carboxylic acid

HRID 860729Notes

Reaction equation

HRID 860729 reaction equation
C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:37]([OH:39])=[O:38])[CH:35]=2)[C:30]([CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:29]1)(O)=[O:22]>O>[CH:40]1([C:30]2[C:31]3[C:36](=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=3)[N:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:21](=[O:22])[C:29]=23)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 565906291-(4-carboxybutyl)-3-cyclohexyl-1H-indole-6-carboxylic acid

Product 1

HCID 5659063011-Cyclohexyl-10-oxo-7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole-3-carboxylic acidYield 118.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of TFA (1.0 mL) and TFAA (469 mg, 2.232 mmol) was added dropwise to 1-(4-carboxybutyl)-3-cyclohexyl-1H-indole-6-carboxylic acid (365 mg, 1.063 mmol) at 0° C. The reaction mixture was then warmed to rt. and stirred for 4 hr. Water was then added slowly to quench the reaction and a precipitate formed. This was collected by filtration to provide the product as a yellow-greenish solid, (410 mg, >100% yield). MS m/z 326(MH+); 1H NMR (500 MHz, CD3OD) □ ppm 1.39–1.50 (m, 3 H) 1.73–2.14 (m, 11 H) 2.88 (m, 2 H) 3.45 (m, 1 H) 4.46 (m, 2 H) 7.73 (dd, J=8.54, 1.22 Hz, 1 H) 7.98 (d, J=8.55 Hz, 1 H) 8.21 (s, 1 H).

Workup

  1. customto quench
  2. customthe reaction
  3. customa precipitate formed
  4. filtrationThis was collected by filtration

Sources & evidence

ORD record
ord-276c533671754c03b48bd3cb6ae806c7
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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