Potassium Hydroxide → HCID 59455042, compound

HRID 1400407Notes

Reaction equation

HRID 1400407 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(O)[CH2:13][CH2:14][CH2:15][CH3:16])[C:6]3[CH2:25][CH2:26][N:27]([CH3:29])[CH2:28][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+]>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)\[CH2:13][CH2:14][CH2:15][CH3:16])[C:6]3[CH2:25][CH2:26][N:27]([CH3:29])[CH2:28][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 49779594HCID 49779594, compound

Product 1

HCID 59455042HCID 59455042, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

1-(8-Chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(4-fluorophenyl)hexan-2-ol (800 mg, 1.8 mmol) was dissolved in thionyl chloride (5 mL) and the solution was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methyl-2-pyrrolidone, stirred for 5 min. at RT, powdered KOH (725 mg, 1.2 mmol) added, and then heated at 100° C. for 3 h. The reaction mixture was cooled to RT and diluted with ice-water to obtain solid product which was filtered and washed with hexane. The product was purified by HPLC. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 7.70 (m, 2H), 7.50 (m, 1H), 7.36 (m, 2H), 7.0 (m, 2H), 6.85 (m, 1H), 4.40 (m, 2H), 4.20 (m, 2H), 3.60 (m, 1H), 3.50 (m, 1H), 3.38 (m, 1H), 3.05 (m, 1H), 2.90 (s, 3H), 2.70 (m, 1H), 2.30 (m, 1H), 1.35 (m, 2H), 0.9 (t, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in N-methyl-2-pyrrolidone
  3. stirringstirred for 5 min. at RT
  4. temperatureheated at 100° C. for 3 h
  5. temperatureThe reaction mixture was cooled to RT
  6. customto obtain solid product which
  7. filtrationwas filtered
  8. washwashed with hexane
  9. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-f4ac6ba40dc04016b6455f3317c74423
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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