3-Pyridinecarboxaldehyde → HCID 59191283, compound

HRID 626053Notes

Reaction equation

HRID 626053 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1.[BH4-].[Na+]>CO>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11]([NH:12][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 59191245HCID 59191245, compound

Product 1

HCID 59191283HCID 59191283, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To 4-(4-ethyl-2-methoxyphenoxy)-3-fluoroaniline (261.2 mg, 1 mmol) were added methanol (4 mL) and nicotinaldehyde (120 μL, 1.2 mmol). The reaction was stirred at 30° C. for 17 h under argon. To the reaction mixture was added NaBH4 (38 mg, 1 mmol). The reaction was stirred at 30° C. for 4 h under argon. The resulting mixture was concentrated in vacuo, dissolved in dichloromethane, washed with a saturated solution of NH4Cl and extracted with dichloromethane. Combined organic phases were dried over Na2SO4, concentrated in vacuo, to give the title product as a yellow oil (160.5 mg; 46%), after purification by preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. stirringThe reaction was stirred at 30° C. for 4 h under argon
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutiondissolved in dichloromethane
  4. washwashed with a saturated solution of NH4Cl
  5. extractionextracted with dichloromethane
  6. dry with materialCombined organic phases were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbd53927684741b386037f88e3feba3c
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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