Triethylamine → tert-Butyl (2E)-3-(3-aminopyridin-2-yl)acrylate

HRID 217653노트

반응식

HRID 217653 반응식
[NH2:1][C:2]1[C:3](Br)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH:10]=[CH2:11].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:3](/[CH:11]=[CH:10]/[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 6428163-Amino-2-bromopyridine

생성물 1

HCID 59168063tert-Butyl (2E)-3-(3-aminopyridin-2-yl)acrylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

950 mg (4.94 mmol) of the bromide from Example 5A, 1900 mg (14.83 mmol) of tert-butyl acrylate, 330 mg (1.50 mmol) of palladium(II) acetate, 450 mg (1.50 mmol) of tri-ortho-tolylphospine are dissolved in 15 ml of acetonitrile, and 1000 mg (9.88 mmol) of triethylamine are added. The mixture is stirred under reflux for 16 h. The reaction mixture is concentrated, mixed with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate, filtered, concentrated and purified by column chromatography on silica gel with cyclohexane/ethyl acetate (7:3). 95 mg (6% of theory) of product are obtained.

후처리

  1. temperatureunder reflux for 16 h
  2. concentrationThe reaction mixture is concentrated
  3. additionmixed with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography on silica gel with cyclohexane/ethyl acetate (7:3)
  9. custom95 mg (6% of theory) of product are obtained

출처 및 근거

ORD 기록
ord-cb63c1bf778e49f4bcd0b8a50b47bb81
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198282B2

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