Sodium hydride → HCID 131728135, compound

HRID 2239598Notes

Reaction equation

HRID 2239598 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=1>>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:3][CH2:2][O:1][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 131728135HCID 131728135, compoundYield 37%

Conditions

Temperature
100 °C

Procedure

Tert-Butyl (2-hydroxyethyl)carbamate (8.88 g, 55.08 mmol) was added to a solution of NaH (55%, 55.08 mmol, washed twice with petroleum ether) in DMF (150 ml) at −10° C. and stirred for 10 mins. 2-Chloro-5-(trifluoromethyl)pyridine (10.0 g, 55.08 mmol) was added and the reaction mixture was stirred at rt for 3 days, heated to 100° C. and cooled to rt. The reaction mixture was evaporated, the residue was washed with isopropylether, and the solution was decanted from insoluble salts and concentrated. The residue was dissolved in EtOAc, washed twice with water, dried over MgSO4 and concentrated. Recrystallisation from isobutylethyl ether gave the title compound (6.2 g, 37%). 1H-NMR (500 MHz, CDCl3) δ 1.46 (s, 9H), 3.56 (br.m, 2H), 4.45 (t, 2H), 6.84 (d, 1H), 7.79 (dd, 1H), 8.44 (s, 1H.

Workup

  1. washwashed twice with petroleum ether) in DMF (150 ml) at −10° C.
  2. stirringthe reaction mixture was stirred at rt for 3 days
  3. temperaturecooled to rt
  4. customThe reaction mixture was evaporated
  5. washthe residue was washed with isopropylether
  6. customthe solution was decanted from insoluble salts
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in EtOAc
  9. washwashed twice with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated
  12. customRecrystallisation from isobutylethyl ether

Sources & evidence

ORD record
ord-71c5f6b0d1e64858914781972be2c7c8
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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