2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 11407971, compound

HRID 724489Notes

Reaction equation

HRID 724489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([OH:24])=[N:12][CH:13]=[CH:14]2)=[N:9]1.FC(F)(F)S(O[CH2:31][C:32]([F:35])([F:34])[F:33])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11](=[O:24])[N:12]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH:13]=[CH:14]2)=[N:9]1

Participants

4

Reactant 2

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178517606HCID 178517606, compound

Product 1

HCID 11407971HCID 11407971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-chlorophenyl)-3-(4-chlorophenyl)-2H-pyrazolo[3,4-c]pyridin-7-ol (I-9A-1b: 150 mg, 0.421 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (107 mg, 0.463 mmol) and CS2CO3 (151 mg, 0.463 mmol) in DMF (2.1 ml) were stirred overnight at room temperature. The reaction mixture was extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), concentrated in vacuo, and then purified on a Biotage™ Flash 12M column using 0–40% ethyl acetate in hexanes as eluant to give the title compound 9A-1 (145 mg, 79%) as a colorless solid: +ES MS (M+1) 438.3; 1H NMR (CD2Cl2) δ 7.70 (d, J=6.2 Hz, 1H), 7.59–7.56 (m, 1H), 7.52–7.43 (m, 3H), 7.38–7.34 (m, 2H), 7.29–7.25 (m, 3H), 5.03 (br s, 2H).

Workup

  1. extractionThe reaction mixture was extracted from saturated aqueous NaHCO3 with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified on a Biotage™ Flash 12M column

Sources & evidence

ORD record
ord-98eabae1dd2b49de895381518209f361
Source dataset
uspto-grants-2006_11
Patent number
US07141669B2

Reaction notes

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