Potassium Hydroxide → HCID 59455101, compound

HRID 1401481Notes

Reaction equation

HRID 1401481 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([CH:21]3[CH2:24][CH2:23][CH2:22]3)([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)O)[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.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](\[CH:21]3[CH2:22][CH2:23][CH2:24]3)/[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:6]3[CH2:25][CH2:26][N:27]([CH3:29])[CH2:28][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 49779651HCID 49779651, compound

Product 1

HCID 59455101HCID 59455101, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

2-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-cyclobutyl-1-(4-fluorophenyl)ethanol (500 mg, 1.2 mmol) was dissolved in thionyl chloride (5 mL) and the solution was stirred at RT for 3 h. Excess thionyl chloride was removed under reduced pressure and the residue was dissolved in N-methyl-2-pyrrolidone (3 mL) and the solution was stirred for 5 min. at RT. Powdered KOH (637 mg, 11 mmol) was added and the reaction mixture was heated at 100° C. for 3 h. The reaction mixture was cooled to RT and diluted with water. The precipitate obtained was filtered and washed with hexane, followed by purification by HPLC. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 7.58 (m, 1H), 7.45 (d, 1H), 7.25 (m, 1H), 7.10 (d, 1H), 7.0 (m, 3H), 6.70 (m, 1H), 4.30-4.20 (m, 3H), 3.65 (m, 2H), 3.50 (m, 2H), 2.90 (m, 2H), 2.80 (s, 3H), 2.20 (m, 2H), 1.80 (m, 1H), 1.60-1.30 (m, 1H).

Workup

  1. customExcess thionyl chloride was removed under reduced pressure
  2. dissolutionthe residue was dissolved in N-methyl-2-pyrrolidone (3 mL)
  3. stirringthe solution was stirred for 5 min. at RT
  4. temperaturethe reaction mixture was heated at 100° C. for 3 h
  5. temperatureThe reaction mixture was cooled to RT
  6. customThe precipitate obtained
  7. filtrationwas filtered
  8. washwashed with hexane
  9. customfollowed by purification by HPLC

Sources & evidence

ORD record
ord-75828a18fad74ae3aefeb14f87f0b967
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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