Trifluoroacetic anhydride → HCID 23042861, compound

HRID 2165534Notes

Reaction equation

HRID 2165534 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]1([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]([NH2:29])=O)=[CH:19]2)[CH2:16][CH2:15]1>O1CCOCC1.C(N(CC)CC)C.ClCCl>[CH:14]1([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]#[N:29])=[CH:19]2)[CH2:15][CH2:16]1

Participants

6

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 23042866HCID 23042866, compound

Product 1

HCID 23042861HCID 23042861, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic anhydride (19.5 g) was added dropwise to a cooled (0° C.), stirred solution of 1-cyclopropylmethyl-1H-indole-3-carboxamide (5 g) in dioxane (100 ml) and triethylamine (18 g). After the addition the mixture was stirred at room temperature for two hours, the mixture was diluted with dichloromethane (200 ml) and washed with water (3×100 ml), dried (Na2SO4) and evaporated at reduced pressure. The residue was purified by column chromatography on silica eluting with dichloromethane to afford a colourless oil, (5 g); δH (CDCl3, 60 MHz) 0.3-0.6 (4H, m, 2×CH2), 0.9 (1H, m, CH), 4.0 (2H, d, J=7, CH2), 7.0-7.7 (5H, m); νmax 2210 (C≡N).

Workup

  1. additionAfter the addition the mixture
  2. washwashed with water (3×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated at reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with dichloromethane
  6. customto afford a colourless oil, (5 g)

Sources & evidence

ORD record
ord-a5bfe6528b3a4da6ab47f3259ad09f82
Source dataset
uspto-grants-1990_07
Patent number
US04940703

Reaction notes

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