Sodium Carbonate → Ethyl[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]acetate

HRID 603507Notes

Reaction equation

HRID 603507 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH3:14])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.O1CCOCC1>C1(C)C=CC=CC=1.O>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH3:14])=[CH:4][CH:3]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 201262(4-Methoxyphenyl)boronic acidHCID 59300476Ethyl 2-(6-chloro-3-methylpyridin-2-YL)acetate

Product 1

HCID 59300475Ethyl[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Following the same procedure described for Example 472 (Step 1) and starting from ethyl (6-chloro-3-methyl-2-pyridinyl)acetate (Example 478, 0.20 g, 0.94 mmol), Na2CO3 (0.24 g, 2.24 mmol), 4-methoxyphenyl boronic acid (0.57 g, 3.74 mmol), and PdCl2(dppf)CH2Cl2 (0.15 g, 0.19 mmol) in a mixture of toluene (1.50 mL), 1,4-dioxane (0.50 mL) and water (0.60 mL), the title compound was obtained (0.25 g, 94%). 1H NMR (400 MHz, CD2Cl2) δ 7.95 (d, 2H), 7.53 (s, 2H), 6.98 (d, 2H), 4.20 (q, 2H), 3.92 (s, 2H), 3.86 (s, 3H), 2.33 (s, 3H), 1.29 (t, 3H).

Sources & evidence

ORD record
ord-32dc4430374749c58e4b8111d806a95b
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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