Heptane → HCID 11673096、化合物

HRID 1921379ノート

反応式

HRID 1921379 の反応式
CC1(C)C(C)(C)C=[N:5][C:4](B2OCCO2)=C1.[C:16](=[O:19])([O-])[O-].[K+].[K+].Br[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O.C(OCC)(=O)C.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]>[CH2:29]([C:30]1[C:4]([O:19][CH3:16])=[N:5][C:33]([CH3:34])=[C:32]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:31]=1)[CH3:28]

参加物

8

反応物 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

生成物 1

HCID 11673096HCID 11673096、化合物収率 94%

試薬・触媒・溶媒 3

HCID 178478476HCID 178478476、化合物触媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
107.5 °C

実験手順

Under a nitrogen atmosphere, a three neck round bottom flask is charged with 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (7.8 g, 28.14 mmol) as prepared above, potassium carbonate (9.72 g, 70.33 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane (1.23 mg, 1.68 mmol) followed by anhyd dimethylformamide (100 mL). To this is added a solution of 2-bromothiophene (9.2 g, 56.44 mmol) in dimethylformamide (10 mL) and the resulting mixture is heated to 105-110° C. for 16 hr. The reaction is cooled, diluted with ethyl acetate and washed with water, with brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography eluting with heptane, then heptane-5% ethyl acetate to afford 3-ethyl-2-methoxy-6-methyl-5-(thiophen-2-yl)pyridine as a yellow oil (94% yield).

後処理

  1. temperatureThe reaction is cooled
  2. washwashed with water, with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with heptane

出典と根拠

ORDレコード
ord-b82d2388aee24862b1c66dc077e0cfd6
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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