Water → 5-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

HRID 1929802Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester (8.7 g, 29 mmol) was dissolved in toluene (85 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (1.2 g, 1.4 mmol), 4-chlorophenylboronic acid (4.9 g, 29 mmol) and sodium carbonate solution (2M, 30 mL). This mixture was heated to 90° C. for 1.5 h and cooled to room temperature. Water (150 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3) to give the title compound (5.3 g) as a pinkish solid; MS (ISP) 322.1 (M+H)+.

Workup

temperaturecooled to room temperature
customthe phases were separated
extractionthe water mixture was extracted with ethylacetate
dry with materialdried with MgSO4
customthe volatiles removed in vacuo
customThe residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3)

Sources & evidence

ORD record: ord-a77265ccec1c40ac81b74ad13c40d9da
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188093B2

Reaction notes

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