Potassium Carbonate → 6-(2,3,6-Trifluoro-4-formyl-phenoxy)-nicotinonitrile

HRID 492576Notes

Reaction equation

[F:1][C:2]1[C:9]([F:10])=[C:8]([OH:11])[C:7]([F:12])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>>[F:10][C:9]1[C:2]([F:1])=[C:3]([CH:4]=[O:5])[CH:6]=[C:7]([F:12])[C:8]=1[O:11][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 51520946-Chloro-3-pyridinecarbonitrile

HCID 451201142,3,5-Trifluoro-4-hydroxybenzaldehyde

Product 1

HCID 859574986-(2,3,6-Trifluoro-4-formyl-phenoxy)-nicotinonitrileYield 57.8%

Procedure

Using a method similar to Example 710, Part 2, using 2,3,5-trifluoro-4-hydroxy-benzaldehyde (1.00 g, 5.64 mmol), 6-chloronicotinonitrile (782 mg, 5.64 mmol) and K2CO3 (1.17 g, 8.47 mmol) gives 6-(2,3,6-trifluoro-4-formyl-phenoxy)-nicotinonitrile (907 mg) contaminated with 6-chloronicotinonitrile starting material. Dissolve this mixture in MeOH (15 ml) and treat with isoamylamine (194 mg, 2.23 mmol). After stirring for two hours, add NaBH4 (105 mg, 2.79 mmol) and stir for an additional hour. Purification as described in Example 710, Step 4, gives 6-{2,3,6-trifluoro-4-[(3-methyl-butylamino)-methyl]-phenoxy}-nicotinonitrile (383 mg) as a colorless oil.

Sources & evidence

ORD record: ord-d4b62ea894094adcbd2106940d445276
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531557B2

Reaction notes

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