Sodium hydride → HCID 68842009, compound

HRID 1454887Notes

Reaction equation

HRID 1454887 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[CH2:11][C:12]1[N:17]=[C:16]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19]([NH:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:11][O:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])[N:17]=1)=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1375123,3,3-Trifluoro-1-propanolHCID 68845579N-(6-chloromethyl-pyridin-2-yl)-2,2-dimethyl-propionamide2×

Product 1

HCID 68842009HCID 68842009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,3,3-Trifluoro-propan-1-ol (0.214 g) in THF (8 mL) was treated under an argon atmosphere with sodium hydride (0.1 g, 60% suspension in oil) and stirred for 1 h at RT. N-(6-chloromethyl-pyridin-2-yl)-2,2-dimethyl-propionamide, 0.142 g, product of example 120 step A], was added and the mixture was heated at 85° C. for 2.5 h. The reaction mixture was cooled, partitioned between ice water and AcOEt, the layers were separated, the organic layer dried over Na2SO4, filtered and evaporated to give 2,2-dimethyl-N-[6-(3,3,3-trifluoro-propoxymethyl)-pyridin-2-yl]-propionamide (0.21 g) as a light brown oil. MS (ESI): 305.3 (MH+).

Workup

  1. temperaturethe mixture was heated at 85° C. for 2.5 h
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ice water and AcOEt
  4. customthe layers were separated
  5. dry with materialthe organic layer dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4db7f07884114b4f887f51414fc1e4be
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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