Sodium borohydride → HCID 58614630, compound

HRID 923013Notes

Reaction equation

HRID 923013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1[C:22]1[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][N:23]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1[C:22]1[CH:31]=[CH:30][C:25]([CH2:26][OH:27])=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58614857HCID 58614857, compound

Product 1

HCID 58614630HCID 58614630, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 110 mg of methyl 6-(2-chloro-5-(2-methyl-6-(trifluoromethyl)nicotinamido)phenyl)nicotinate at 0° C. in 5 mL of EtOH was slowly added 148 mg of Sodium Borohydride. The reaction was subsquently refluxed for 1 hour until complete, quenched with water and extracted with Ethyl Acetate. The organic layer was dried over Magnesium Sulfate, filtered, concentrated and purified by reverse phase HPLC to give pure N-(4-chloro-3-(5-(hydroxymethyl)pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide. MS (Q1) 422.1 (M)+.

Workup

  1. customat 0° C.
  2. temperatureThe reaction was subsquently refluxed for 1 hour until complete,
  3. customquenched with water
  4. extractionextracted with Ethyl Acetate
  5. dry with materialThe organic layer was dried over Magnesium Sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-9e7777dacd4b4ca89b53bbcd82d7d6a6
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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