Dimethylformamide → 5-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde

HRID 1921310노트

반응식

HRID 1921310 반응식
Br[C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C[C:10]1([CH3:23])[C:15]([CH3:17])(C)[CH:14]=[N:13][C:12](B2OCCO2)=[CH:11]1.[C:24](=[O:27])([O-])[O-].[K+].[K+].CN(C)[CH:32]=[O:33]>O.ClCCl.[Pd].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:10]([C:15]1[CH:17]=[C:7]([C:5]2[O:6][C:2]([CH:24]=[O:27])=[CH:3][CH:4]=2)[C:12]([CH3:11])=[N:13][C:14]=1[O:33][CH3:32])[CH3:23]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

생성물 1

HCID 116228885-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde수율 103%

시약·촉매·용매 2

HCID 178478476HCID 178478476, 화합물촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

To a mixture of 5-bromofuran-2-carbaldehyde (1.25 g, 7.14 mmol), 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (1.32 g, 4.76 mmol), prepared in accordance with one of the procedures of Step 1, PREPARATION 2, potassium carbonate (2.63 g, 7.14 mmol) and dimethylformamide (30 mL) under a nitrogen atmosphere is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane adduct (0.2 g, 6 mol %) and the mixture is stirred at 90° C. for 2 hr. The reaction is cooled, diluted with water and washed with water. The organic layer is separated, dried, filtered and concentrated. The residue is purified by flash chromatography eluting with heptane-30% ethyl acetate to afford 5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde (1.2 g, 103% yield). MS: m/e=246 (M+H). 1H-NMR (CDCl3, δ ppm) 9.64 (s, 1H), 7.79 (s, 1H), 7.33 (d, 1H, J=3.8 Hz), 6.67 (d, 1H, J=3.8 Hz); 3.99 (s, 3H); 2.64 (s, 3H); 2.61 (q, 2H, J=7.6 Hz), 1.21 (t, 3H, J=7.6 Hz).

후처리

  1. temperatureThe reaction is cooled
  2. washwashed with water
  3. customThe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography
  8. washeluting with heptane-30% ethyl acetate

출처 및 근거

ORD 기록
ord-73fab38bd5af43fdb36b09473b8065c0
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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