Sodium Carbonate → tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2223702노트

반응식

HRID 2223702 반응식
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.[Cl-].[Li+].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH:31]=[C:30](S(C(F)(F)F)(=O)=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>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.CCOC(C)=O.C(Cl)Cl.COCCOC>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH:29]=[C:30]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH2:31][CH2:32]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27339582-Methoxyphenylboronic acidHCID 21193094Tert-butyl 4-((trifluoromethyl)sulfonyl)-3,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 21226138Dichloromethane ethylacetate용매

실험 절차

A three necked flask purged with nitrogen is charged with aqueous 2N Na2CO3 (1.4 mL), 1,2-dimethoxyethane (3.7 mL), 2-methoxyphenyl boronic acid (206 mg, 1.35 mmol), anhydrous lithium chloride (123 mg, 2.9 mmol), 4-trifluoromethanesulfonyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (321 mg, 0.96 mmol) and tetrakis(triphenylphosphine)palladium (56 mg, 0.048 mmol). The mixture is stirred at reflux for 2 h under nitrogen, cooled and concentrated under reduced pressure. The residue is partitioned between CH2Cl2 (10 mL), aqueous 2N Na2CO3 (10 mL), and concentrated NH4OH (1 mL). The aqueous layer is extracted twice with CH2Cl2. The combined organic layers are dried (MgSO4), filtered and concentrated to provide a crude oil. Flash chromatography (Hex/AcOEt/CH2Cl2: 5/1/1) provides the title compound.

후처리

  1. customA three necked flask purged with nitrogen
  2. temperatureat reflux for 2 h under nitrogen
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is partitioned between CH2Cl2 (10 mL), aqueous 2N Na2CO3 (10 mL), and concentrated NH4OH (1 mL)
  6. extractionThe aqueous layer is extracted twice with CH2Cl2
  7. dry with materialThe combined organic layers are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide a crude oil

출처 및 근거

ORD 기록
ord-be28a7eec9aa401babc598277d43fdfc
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375227B2

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