Heptane → HCID 11673096, 화합물

HRID 1921379노트

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HRID 1921379 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 11673096HCID 11673096, 화합물수율 94%

시약·촉매·용매 3

HCID 178478476HCID 178478476, 화합물촉매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
107.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b82d2388aee24862b1c66dc077e0cfd6
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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