Sodium borohydride → 6-tert-Butyl-2-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-8-fluorophthalazin-1(2H)-one

HRID 407651Notes

Reaction equation

HRID 407651 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([Cl:25])[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866839152-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-chloronicotinaldehyde

Product 1

HCID 866839406-tert-Butyl-2-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-8-fluorophthalazin-1(2H)-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-chloronicotinaldehyde 103b (2.0 g, 5.5 mmol) in methanol (30 mL) was added NaBH4 (700 mg, 16.5 mmol) at room temperature. The reaction mixture was stirred for 1 h and quenched with water (30 mL). It was then concentrated under reduced pressure and the residue was extracted with dichloromethane (3×30 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 116a as a white solid (1.8 g, 90%). MS: [M+H]+ 362.3.

Workup

  1. customquenched with water (30 mL)
  2. concentrationIt was then concentrated under reduced pressure
  3. extractionthe residue was extracted with dichloromethane (3×30 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-497ba858f217416fae29a3eb5bdd62a5
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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