Sodium hydride → HCID 22464513, compound

HRID 1935455Notes

Reaction equation

HRID 1935455 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][SH:6].Br[C:10]1[C:11]([C:16]#[N:17])=[N:12][CH:13]=[CH:14][CH:15]=1>C1COCC1>[C:16]([C:11]1[C:10]([S:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[CH:15][CH:14]=[CH:13][N:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8176943-Bromopyridine-2-carbonitrileHCID 41339242,2,2-Trifluoroethanethiol

Product 1

HCID 22464513HCID 22464513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of sodium hydride (60% oil dispersion, 180 mg, 4.52 mmol) in dry THF (17 mL) under N2 was treated with trifluoroethanethiol (0.40 mL, 4.52 mmol) and the mixture was heated to 50° C. When gas evolution ceased (ca. 1 h), 3-bromo-2-cyanopyridine was added and the mixture was heated to reflux for 4 h. The solvent wag removed in vacuo and the residue was taken up in CH2Cl2 and filtered to remove precipitated sodium bromide. The filtrate was concentrated at reduced pressure to afford the title compound as an orange oil:

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 h
  4. customThe solvent wag removed in vacuo
  5. filtrationfiltered
  6. customto remove
  7. customprecipitated sodium bromide
  8. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-6a80db5ac5fb4f63b10149045f4cc58f
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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