Acetic Acid → HCID 90010255, compound

HRID 1056612Notes

Reaction equation

HRID 1056612 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.C(O)(=O)C.[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:15]=1[CH:16]=O.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:16][C:15]2[C:14]([F:13])=[CH:21][CH:20]=[CH:19][C:18]=2[F:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1362842,6-DifluorobenzaldehydeHCID 6428116-Bromopyridin-3-amineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 90010255HCID 90010255, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromopyridin-3-amine (500 mg, 2.89 mmol), in MeOH (3 mL), acetic acid (0.165 mL, 2.89 mmol), 2,6-difluorobenzaldehyde (0.31 mL, 2.89 mmol) was added. After stirring the resulting mixture at RT for 12 h, sodium cyanoborohydride (363 mg, 5.78 mmol) was added at 0° C. and resulting mixture was stirred at RT for 6 h. Solvent was evaporated under vacuum. Residue was purified by column chromatography to afford 200 mg (23%) of the title compound as white solid. GC-MS-298, 300 [M+, Br79,81]

Workup

  1. customresulting mixture
  2. stirringwas stirred at RT for 6 h
  3. customSolvent was evaporated under vacuum
  4. customResidue was purified by column chromatography

Sources & evidence

ORD record
ord-05bd00785ea84b4cb70777f7cb81fdd4
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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