Sodium hydride → HCID 66580148, compound

HRID 2368812Notes

Reaction equation

HRID 2368812 reaction equation
[F:1][C:2]([F:7])([F:6])[C@@H:3]([OH:5])[CH3:4].[H-].[Na+].Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>CN(C=O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:5][C@@H:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[N:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 6999971(2S)-1,1,1-Trifluoropropan-2-ol

Product 1

HCID 66580148HCID 66580148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 4-neck flask, commercially available 2-chloro-5-nitropyridine (71.9 g) and (S)-1,1,1-trifluoropropan-2-ol (54.3 g) were dissolved in DMF (610 ml) and sodium hydride (20 g, 55%) was added at a temperature of 16 to 18° C. (ice cooling). Following addition, the mixture was allowed to stir for 1 hour. The mixture was poured into ice and was allowed to hydrolyze. The suspension was warmed to RT over a period of 12 hours and the solid was filtered and washed with additional water and then with a small amount of hexanes (50 mL). The brown solid was further dried in vacuo to provide the title compound. (81.9 g). 1H-NMR (δ, CDCl3): 9.06 (m, 1H), 8.43 (dd, 1H), 6.93 (d, 1H), 5.87 (m, 1H); 1.54 (m, 3H).

Workup

  1. additionaddition
  2. additionThe mixture was poured into ice
  3. filtrationthe solid was filtered
  4. washwashed with additional water
  5. customThe brown solid was further dried in vacuo

Sources & evidence

ORD record
ord-a7fa1ed80f644a5fbf57a9fe1a3ef8ae
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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