Trifluoroacetic acid → HCID 59454954, compound

HRID 1401596Notes

Reaction equation

HRID 1401596 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)(O)[CH3:13])[C:6]3[CH2:21][CH:22]([CH3:26])[N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1.S(Cl)(Cl)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH2:13])[C:6]3[CH2:21][CH:22]([CH3:26])[N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24386Thionyl ChlorideHCID 67312409HCID 67312409, compound

Product 1

HCID 59454954HCID 59454954, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(8-Chloro-2,3-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol (900 mg, 2.43 mmol) was dissolved in 5 mL DCM. To this, thionyl Chloride (2 mL in DCM) was added dropwise at 0° C. and stirred for 2.5 h at RT. After completion of starting material (TLC) excess thionyl chloride and solvent was evaporated under vacuum. The residue was neutralized with saturated solution of Sodium bicarbonate at 0° C. and extracted with EtOAc (3 times). The combined organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated to obtain 720 mg of crude which was subjected to reverse phase chromatography to obtain 80 mg of product as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.70 (d, 2H), 7.95 (d, 2H), 7.55 (s, 1H), 7.42 (d, 1H), 7.20 (d, 1H), 5.85 (s, 1H), 5.30 (s, 2H), 4.78 (s, 1H), 4.70 (m, 1H), 4.40 (m, 1H), 4.10 (m, 1H), 3.85 (m, 1H), 3.05 (s, 3H), 2.95 (m, 1H), 1.50 (m, 2H).

Workup

  1. customAfter completion of starting material (TLC) excess thionyl chloride and solvent was evaporated under vacuum
  2. customwas neutralized with saturated solution of Sodium bicarbonate at 0° C.
  3. extractionextracted with EtOAc (3 times)
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain 720 mg of crude which

Sources & evidence

ORD record
ord-8d3c4cbd6c3c4cc18bb8d6014543255b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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