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

HRID 1911794Notes

Reaction equation

HRID 1911794 reaction equation
FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CN[CH2:8][C:9]1[C:10]([N:16]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH2:17][CH:18]2[CH2:20][CH2:19]2)=[N:11][C:12]([F:15])=[CH:13][CH:14]=1.C(=O)(O)[O-:35].[Na+].N#CBr>CO>[CH:18]1([CH2:17][N:16]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:10]2[C:9]([CH:8]=[O:35])=[CH:14][CH:13]=[C:12]([F:15])[N:11]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58795818HCID 58795818, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-6-fluoro-pyridin-2-yl}-bis-cyclopropylmethyl-amine (302 mg, 0.64 mmol) stirred in methanol (10 mL) was added sodium bicarbonate (139.6 mg, 1.24 mmol). After stirring at room temperature for about 15 minutes, cyanogen bromide (237.5 mg, 1.12 mmol) was added and the solution was allowed to stir at room temperature for about 4 hours. 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 (284 mg, yield: 87%) and was used as is without purification.

Workup

  1. stirringto stir at room temperature for about 4 hours
  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-de21bae025c14f52b030d5abeeff2035
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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