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

HRID 61893

반응식

HRID 61893 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 83681Tris(1,1-dimethylethyl)phosphine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e6f1d85672d846248de4662bd3f783e2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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