Methyl iodide → HCID 86584522, compound

HRID 1017220Notes

Reaction equation

HRID 1017220 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH:22]=[C:23]([OH:25])[CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:10]([F:26])=[C:9]([CH3:27])[C:8]=1[F:28])#[N:2].[C:32](=O)([O-])[O-].[Cs+].[Cs+].IC>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH:22]=[C:23]([O:25][CH3:32])[CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:10]([F:26])=[C:9]([CH3:27])[C:8]=1[F:28])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86584523HCID 86584523, compound

Product 1

HCID 86584522HCID 86584522, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To acetonitrile (5 mL) was added 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]-5-hydroxybenzoic acid, ethyl ester (0.20 g, 0.47 mmol), cesium carbonate (0.31 g, 0.94 mmol), and iodomethane (0.13 g, 0.94 mmol). After stirring for 15 hours the mixture was partitioned with ethyl acetate and water. The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methyl-pyridin-2-yl)oxy]-5-methoxybenzoic acid, ethyl ester; NMR (CDCl3) 7.3 (m, 6), 6.8 (s, 1), 4.4 (q, 2), 3.8 (s, 3), 2.4 (s, 3), 1.4 (t, 3) ppm.

Workup

  1. customwas partitioned with ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a9fc1ec5dbfa4320b20c3dcfc0aaa243
Source dataset
uspto-grants-2002_11
Patent number
US06479485B2

Reaction notes

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