Trifluoroacetic acid → HCID 19761417, compound

HRID 373840Notes

Reaction equation

HRID 373840 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2>C1COCC1>[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[CH:11][C:10]=1[CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19761405HCID 19761405, compound

Product 1

HCID 19761417HCID 19761417, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1.0M, 130 ml) was added dropwise to a solution of 90 ml THF and 90 ml TFA (trifluoroacetic acid) at -5° C., and then 17.93 g 2-(2-amino-4-trifluoromethylphenyl)-1H-indole was added. The resulting solution was stirred at room temperature overnight. The reaction mixture was quenched with water and basified with 50% NaOH. The solution was extracted with Et2O. This organic layer was washed with water and saturated NaCl solution, dried (MgSO4), and concentrated to yield 3.65 g solid. Purification by HPLC and recrystallization from MeOH/water yielded 1.93 g solid, m.p. 152°-154° C.

Workup

  1. customThe reaction mixture was quenched with water and basified with 50% NaOH
  2. extractionThe solution was extracted with Et2O
  3. washThis organic layer was washed with water and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7f63cf597434257bad5a4f81c84e863
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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