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Ethyl isobutyrate → 2-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl ester

HRID 61893
Notes
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Reaction equation

HRID 61893 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[CH:11]([CH3:13])[CH3:12].C1COCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:16]([O:15][C:10](=[O:14])[C:11]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)([CH3:13])[CH3:12])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7342Ethyl isobutyrateHCID 8028TetrahydrofuranHCID 2568102-Bromo-6-methoxypyridineHCID 2733832Lithium hexamethyldisilazane

Product 1

HCID 668349252-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl esterYield 64.4%

Reagents, catalysts & solvents 4

HCID 83681
Tris(1,1-dimethylethyl)phosphine
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-6-methoxypyridine (7.0 g), ethyl isobutyrate (4.75 g), tri t-butylphosphine (300 mg) and Pd2(dba)3 (680 mg) were dissolved in toluene (200 ml) under nitrogen atmosphere, added with THF solution of LiHMDS (1.6 M, 24 ml), and the mixture was stirred at 100° C. for 6 hrs. The reaction mixture was diluted with ethyl acetate (300 ml), and washed three times with 15% brine (200 ml). The organic layer was concentrated under reduced pressure and the resulting residues were purified by silica gel column (n-hexane/ethyl acetate=4/1) to obtain the title compound (5.353 g, yield 60%).

Workup

  1. washwashed three times with 15% brine (200 ml)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residues were purified by silica gel column (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e6f1d85672d846248de4662bd3f783e2
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes