3-(Benzyloxy)pyridine-2-carbaldehyde → HCID 59553907, compound

HRID 1170912Notes

Reaction equation

HRID 1170912 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([CH3:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)=[O:9])=[C:6]([C:22]([F:25])([F:24])[F:23])[N:5]=[CH:4][CH:3]=1.[CH2:26]([O:33][C:34]1[C:35]([CH:40]=O)=[N:36][CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:26]([O:33][C:34]1[C:35]([CH:40]2[NH:1][C:2]3[CH:3]=[CH:4][N:5]=[C:6]([C:22]([F:25])([F:24])[F:23])[C:7]=3[C:8](=[O:9])[N:10]2[CH:11]([CH3:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)=[N:36][CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 133745943-(Benzyloxy)pyridine-2-carbaldehydeHCID 595538824-Amino-N-[2-(3,4-difluorophenyl)-1-methylethyl]-2-(trifluoromethyl)-3-pyridinecarboxamide

Product 1

HCID 59553907HCID 59553907, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

4-amino-N-(1-(3,4-difluorophenyl)propan-2-yl)-2-(trifluoromethyl)nicotinamide (3.61 g, 10.05 mmol) and 3-(benzyloxy)picolinaldehyde (2.57 g, 12.1 mmol) were combined along with a catalytic amount of 4-toluenesulfonic acid (0.03 g, 0.20 mmol) in anhydrous toluene (150 mL). This was heated at reflux overnight in a round bottom flask fitted with a Dean-Stark trap. The resultant dark solution was cooled to room temperature, concentrated in vacuo to a dark brown oil. This oil was purified by silica gel column chromatography using 30% acetone/hexanes as eluant to provide the product diastereomers as an oil (4.61 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ 8.2 (m, 1H), 8.0 (m, 1H), 7.3-7.6 (m, 7H), 5.15 (d, 2H), 3.0 (dd, 1H), 2.8 (m, 1H), 1.25 (d, 3H). MS m/z 555.2 (M+H)+.

Workup

  1. temperatureThis was heated
  2. temperatureat reflux overnight in a round bottom flask
  3. customfitted with a Dean-Stark trap
  4. concentrationconcentrated in vacuo to a dark brown oil
  5. customThis oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cbe207aa22294cfe8aead07527d99ba1
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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