1,1,1-Trifluoro-2-propanol → HCID 25129833, compound

HRID 454871Notes

Reaction equation

HRID 454871 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]([OH:5])[CH3:4].[H-].[Na+].[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](Cl)=[N:16][N:15]=[CH:14]2>C1COCC1.CN(C=O)C>[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([O:5][CH:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[N:16][N:15]=[CH:14]2

Participants

5

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 24758Sodium hydrideHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 25129833HCID 25129833, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 1,1,1,-trifluoro-2-propanol (4.0 mL, 44 mmol) in 60 mL of 5:1 THF/DMF was added sodium hydride (60% wt. dispersion in mineral oil, 0.754 g, 33 mmol) resulting in gas evolution. After 20 min, 6-bromo-1-chlorophthalazine (2.62 g, 11 mmol) was added as a solid resulting in a red solution. The reaction was allowed to warm to RT for 1 h. The mixture was quenched with saturated solution of NaHCO3, and extracted with EtOAc (3×). The combined organic layers were evaporated onto silica gel and purified by flash chromatography (ISCO 120 g column, eluting with 25-75% EtOAc in hexanes) to give the title compound as an orange amorphous solid. MS (ESI, pos. ion) m/z: M+1=321.0, 323.0

Workup

  1. customresulting in gas evolution
  2. customresulting in a red solution
  3. customThe mixture was quenched with saturated solution of NaHCO3
  4. extractionextracted with EtOAc (3×)
  5. customThe combined organic layers were evaporated onto silica gel
  6. custompurified by flash chromatography (ISCO 120 g column, eluting with 25-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2ae5209f3d534e168a0dc496bb2477c1
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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