Phosphorus oxychloride → HCID 68538794, compound

HRID 1441266Notes

Reaction equation

HRID 1441266 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[N:14]([CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH:13]=[C:12]2[C:23]([NH2:25])=O>CN(C)C=O>[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[N:14]([CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH:13]=[C:12]2[C:23]#[N:25]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 68538635HCID 68538635, compound

Product 1

HCID 68538794HCID 68538794, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (9.6 ml, 103 mmol) was added dropwise, via a pressure equalising funnel, to a cooled (5-10° C.) solution of 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carboxylic acid amide (20.0 g, 68.3 mmol) in dimethylformamide (200 ml). Following complete addition of phosphorus oxychloride the reaction was left to stir for 10 mins before warming to room temperature and allowing to stir for a further 30 mins. The reaction mixture was then poured carefully into ice cold water (2000 ml), the resulting precipitate filtered off and washed with water. The filter cake was then dissolved in dichloromethane, washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo. The resulting solid was crystallised from diethyl ether to yield 7-chloro-1-(tetrahydro-pyran-4-yl)methyl-1H-indole-3-carbonitrile (12.9 g, 46.9 mmol) as a white solid.

Workup

  1. waitwas left
  2. stirringto stir for a further 30 mins
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with water
  5. dissolutionThe filter cake was then dissolved in dichloromethane
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed in vacuo
  9. customThe resulting solid was crystallised from diethyl ether

Sources & evidence

ORD record
ord-d7c12827d05d43359957d0b0a954fe5b
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

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