2,2,2-Trifluoroethanol → HCID 59726030, compound

HRID 422543Notes

Reaction equation

HRID 422543 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](Cl)=[N:15][N:14]=[CH:13]2.[NH4+].[Cl-]>C1COCC1.CN(C=O)C>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[N:15][N:14]=[CH:13]2

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 59726030HCID 59726030, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,2-trifluoroethanol (329 mg, 3.28 mmol) in 3.0 mL of THF and 3.0 mL of DMF at 0° C. was treated with sodium hydride (60% wt) (131 mg, 3.28 mmol) and the resulting mixture was stirred for 10 min, then solid 6-bromo-1-chlorophthalazine (400 mg, 1.64 mmol) was added in one portion. The mixture was stirred at RT for 1 h, poured into iced-cold saturated NH4Cl solution, and extracted with EtOAc twice. The combined organic layers were dried over sodium sulfate, concentrated under vacuum. The residue was put on an ISCO 40 g column (eluted with 20-70% EtOAc in Hexanes) and purified to give title compound as a tan amorphous solid. MS (ESI, pos. ion) m/z: 309.0 (M+1).

Workup

  1. stirringThe mixture was stirred at RT for 1 h
  2. extractionextracted with EtOAc twice
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washThe residue was put on an ISCO 40 g column (eluted with 20-70% EtOAc in Hexanes)
  6. custompurified

Sources & evidence

ORD record
ord-7d885bf402f44a5abe70716b456a448b
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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