Phosphorus oxychloride → HCID 21880588, compound

HRID 899312Notes

Reaction equation

HRID 899312 reaction equation
C([N:8]1[CH:13]=[CH:12][C:11]2=[C:14]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[N:16]=[C:10]2[C:9]1=O)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:9]1[C:10]2=[N:16][N:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:14]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)=[C:11]2[CH:12]=[CH:13][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11178322HCID 11178322, compound

Product 1

HCID 21880588HCID 21880588, compoundYield 77%

Procedure

A stirred suspension of 6-benzyl-2-(2-chlorophenyl)-3-(4-chlorophenyl)-2H-pyrazolo[3,4-c]pyridin-7(6H)-one (1A-3, 925 mg, 2.07 mmol) in POCl3 (20 ml) was heated at reflux for 5 days. After the reaction was cooled and concentrated, in vacuo, an ethyl acetate solution of the residue was washed with saturated aqueous NaHCO3 and then brine. The solution was dried (Na2SO4), concentrated, in vacuo, and then purified on a Biotage™ Flash 40S column using 0-40% ethyl acetate in hexanes to afford I-9A-1a as an off-white solid (600 mg, 77%): +ESI MS (M+1) 374.3; 1H NMR (400 MHz, CD2Cl2) δ 8.00 (d, J=6.2 Hz, 1H), 7.60-7.45 (m, 5H), 7.38 (d, J=8.7 Hz, 2H), 7.27 (d, J=8.7 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 days
  3. temperatureAfter the reaction was cooled
  4. concentrationconcentrated, in vacuo
  5. washan ethyl acetate solution of the residue was washed with saturated aqueous NaHCO3
  6. dry with materialThe solution was dried (Na2SO4)
  7. concentrationconcentrated, in vacuo
  8. custompurified on a Biotage™ Flash 40S column

Sources & evidence

ORD record
ord-587372b3515b47728e350b0925fbad5d
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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