Trifluoroacetic acid → HCID 18675457, compound

HRID 1635033Notes

Reaction equation

HRID 1635033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18675458HCID 18675458, compound

Product 1

HCID 18675457HCID 18675457, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(3-Chlorophenyl)indole (5.30 g, 23.3 mmol) was dissolved in 50 mL of 1 M BH3 in THF. The mixture was cooled to about 0° C. To the solution was added slowly TFA (50 mL). After addition, the solution was stirred for about 10 minutes. To the solution was added slowly 1M BH3 in THF (40 mL). The mixture was stirred for about 5 minutes and then concentrated in vacuo. The residue was purified by column chromatography on silica, eluting with EtOAc/hexane 1:6. The title compound was obtained as an oil (Yield; 3.93 g, 74%). Rf=0.20 (Silica, EtOAc/hexane 1:4) MS (ES): 229.1; Calc. MW=229.7.)

Workup

  1. additionAfter addition
  2. stirringThe mixture was stirred for about 5 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica
  5. washeluting with EtOAc/hexane 1:6

Sources & evidence

ORD record
ord-b5e54384592641af84968612d9142a4e
Source dataset
uspto-grants-2003_01
Patent number
US06509336B1

Reaction notes

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