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Potassium Carbonate → 3-[3-(6-Cyclopropyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

HRID 1767594
ノート
印刷プレビュー

反応式

HRID 1767594 の反応式
[C:1]([C:3]1[CH:4]=C(B(O)O)C=C[CH:8]=1)#N.Br[C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[CH2:21][CH2:20]2)=[N:17][CH:18]=1.Br[C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25]N=1.[Cl-].[CH:31]1([Zn+])[CH2:33][CH2:32]1.[C:35]([O-:38])(O)=[O:36].[Na+].C([O-])([O-])=[O:41].[K+].[K+]>C1COCC1.C1(C)C=CC=CC=1.CCO.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:3]([O:38][C:35](=[O:36])[CH2:25][C:26]([C:27]1[CH:33]=[CH:31][CH:32]=[C:23]([C:13]2[CH:18]=[N:17][C:16]([CH:19]3[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH:28]=1)=[O:41])([CH3:4])([CH3:8])[CH3:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

13

反応物 6

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 516892Sodium BicarbonateHCID 27343253-Cyanophenylboronic acidHCID 223177225-Bromo-2-cyclopropylpyridineHCID 178479835HCID 178479835、化合物

生成物 1

HCID 69489384
3-[3-(6-Cyclopropyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

試薬・触媒・溶媒 6

HCID 178418397HCID 178418397、化合物触媒2 回HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Compound K7 was obtained from 3-(6-cyclopropyl-pyridin-3-yl)-benzonitrile [prepared by the following procedure: A mixture of 3-cyanophenylboronic acid [CAS-No. 150255-96-2] (8.82 g, 60 mmol), crude 5-bromo-2-cyclopropylpyridine {prepared by the following procedure: A mixture of 2,5-dibromopyridine (11.85 g, 50 mmol), cyclopropyl zinc chloride (0.4 M in THF, 160 mL, 64 mmol), Pd(PPh3)4 (578 mg, 1 mol %) in THF (55 mL) was stirred under Argon atmosphere at 70° C. for 1.5 h. Cooled to RT, poured into sat. NaHCO3-solution, extracted with ether, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown oil (12.36 g).} (ca. 60 mmol), Pd(PPh3)4 (1.733 g, 3 mol %) and K2CO3 (13.82 g, 100 mmol) in toluene (250 mL), EtOH (22 mL) and H2O (50 mL) was stirred at 80° C. for 14 h. Cooled to RT, diluted with EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown solid, which was purified by silica gel column chromatography with cyclohexane/-EtOAc.] (9.88 g, 44.87 mmol) by treatment with tert-butyl bromoacetate and activated zinc, followed by hydrolysis with 10% HCl according to general procedure K (method d).

後処理

  1. customprepared by the following procedure
  2. customprepared by the following procedure
  3. temperatureCooled to RT
  4. extractionextracted with ether
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft a brown oil (12.36 g)
  9. temperatureCooled to RT
  10. washwashed with sat. NaHCO3-solution and brine
  11. dry with materialdried over Na2SO4
  12. customRemoval of the solvent in vacuum
  13. waitleft a brown solid, which
  14. customwas purified by silica gel column chromatography with cyclohexane/-EtOAc
  15. custom] (9.88 g, 44.87 mmol) by treatment with tert-butyl bromoacetate and activated zinc, followed by hydrolysis with 10% HCl according to general procedure K (method d)

出典と根拠

ORDレコード
ord-c7825db3a5d94716b1727c4a690217cc
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07235547B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート