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

HRID 2223702ノート

反応式

HRID 2223702 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be28a7eec9aa401babc598277d43fdfc
出典データセット
uspto-grants-2008_05
特許番号
US07375227B2

反応ノート

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