Sodium borohydride → HCID 58614630, compound

HRID 633164Notes

Reaction equation

HRID 633164 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 subsequently 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 subsequently 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-8b12e68a290148eb806a36bc4a8be160
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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