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Hexane → 6-(2,6-Diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester

HRID 1392624
Notes
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Reaction equation

HRID 1392624 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7](Cl)=[N:6][CH:5]=1.[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:17]=1B(O)O)[CH3:15].C([O-])([O-])=O.[Na+].[Na+].CCCCCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:17]2[C:18]([CH2:22][CH3:23])=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:14][CH3:15])=[N:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 18437832(2,6-Diethylphenyl)boronic acidHCID 22498691Methyl 6-chloro-4-methoxypyridine-3-carboxylate

Product 1

HCID 596780886-(2,6-Diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloro-4-methoxy-nicotinic acid methyl ester (4.0 g, 19.8 mmol), 2,6-diethylphenyl boronic acid (7.0 g, 39.3 mmol), Na2CO3 (2M in H2O, 39 mL) and Pd(PPh3)4 (2.0 g, 1.7 mmol) in toluene (200 mL) is heated overnight at 80° C. under argon. On cooling, hexane (200 mL) is added and the organic layer separated. The organic layer is washed with 1N NaOH and water, dried (Na2SO4) and concentrated. The residue is purified by silica gel column (hexane/EtOAc 4:1) to give 6-(2,6-diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester. 1H NMR (CDCl3) 8.99 (s, 1H), 7.30 (m, 1H), 7.15 (d, 2H), 6.89 (s, 1H), 3.95 (s, 3H), 3.94 (s, 3H), 2.34 (m, 4H), 1.06 (t, 6H).

Workup

  1. temperatureOn cooling
  2. customthe organic layer separated
  3. washThe organic layer is washed with 1N NaOH and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-f838468697874cb7bf109d0a61747029
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342115B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes