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

HRID 1921308ノート

反応式

HRID 1921308 の反応式
Br[C:2]1[S: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[S: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]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 784285-Bromothiophene-2-carbaldehydeHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

生成物 1

HCID 115217765-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)thiophene-2-carbaldehyde収率 103%

試薬・触媒・溶媒 2

HCID 178478476HCID 178478476、化合物触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 5-bromothiophene-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, 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)thiophene-2-carbaldehyde (1.2 g, 103% yield).

後処理

  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

出典と根拠

ORDレコード
ord-1830d4710f894fcfbb63abaa4c9aba6a
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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