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

HRID 228422Notes

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-87d77f543ebd4e30a05909fa34a944cb
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560463B2

Reaction notes

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