Water → 2-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

HRID 1911795Notes

Reaction equation

HRID 1911795 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:6]2[C:11]([CH2:12]N(CC3C=C(C(F)(F)F)C=C(C(F)(F)F)C=3)C#N)=[CH:10][CH:9]=[C:8]([F:31])[N:7]=2)[CH2:3][CH2:2]1.[OH2:36].[N-]=[N+]=[N-].[Na+]>C(O)(C)C.[Br-].[Zn+2].[Br-]>[CH:1]1([CH2:4][N:5]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:6]2[C:11]([CH:12]=[O:36])=[CH:10][CH:9]=[C:8]([F:31])[N:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 58795829HCID 58795829, compound

Product 1

HCID 587957962-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 3776IsopropanolSolvent

Procedure

To [2-(bis-cyclopropylmethy-amino)-6-fluoro-pyridin-3-ylmethyl]-(3,5-bis-trifluoromethyl-benzyl)-cyanamide (244 mg, 0.5 mmol) stirred in isopropanol (5 mL) and water (10 mL) was added sodium azide (38.4 mg, 0.55 mmol) and zinc bromide (115.6 mg, 0.5 mmol). After stirring at reflux overnight, the solution was extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give the title compound as an orange oily product (248 mg, yield: 91%) and was used as is without purification.

Workup

  1. temperatureat reflux overnight
  2. extractionthe solution was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0cb570ffd2c4425db4cb27f56828182a
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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