Trifluoroacetic anhydride → HCID 57935725, compound

HRID 1434573Notes

Reaction equation

HRID 1434573 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].FC(F)(F)[C:14]([O:16]C(=O)C(F)(F)F)=[O:15]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:14]([OH:16])=[O:15])=[CH:5][N:6]2[CH3:11]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 225589374-Bromo-1-methyl-1H-indole

Product 1

HCID 57935725HCID 57935725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-bromo-1-methyl-1H-indole (D16) (7.0 g) in tetrahydrofuran (50 ml) was treated with a solution of trifluoroacetic anhydride (5.65 ml) in tetrahydrofuran (20 ml) at 0° C. The reaction mixture was allowed to warm to room temperature over 6 h, whilst stirring. The reaction mixture was concentrated in vacuo and then re-suspended in ethanol (25 ml). The solution was treated with 5N sodium hydroxide solution (50 ml) and heated under reflux for 18 h. The reaction mixture was washed with diethyl ether and the aqueous phase acidified with 5N hydrochloric acid solution. The precipitate was filtered, washed with water and concentrated in vacuo to afford the title compound (4.88 g). TLC, Silica (cyclohexane-ethyl acetate-acetic acid [3:1:0.1]), Rf=0.35.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe solution was treated with 5N sodium hydroxide solution (50 ml)
  3. temperatureheated
  4. temperatureunder reflux for 18 h
  5. washThe reaction mixture was washed with diethyl ether
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa68587fe3ed44b39deadfcd0591292e
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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