Potassium Carbonate → HCID 70206537、化合物

HRID 2367924ノート

反応式

HRID 2367924 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:27]([O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)([CH3:30])([CH3:29])[CH3:28]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11550568Tert-butyl 6-bromohexanoateHCID 66820850Methyl 6-(3'-hydroxyphenyl)-pyridine-2-carboxylate

生成物 1

HCID 70206537HCID 70206537、化合物収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 6-(3′-hydroxyphenyl)-pyridine-2-carboxylate (7) (600 mg, 2.6 mmol, 1 eq.) and t-butyl 6-bromohexanoate (980 mg, 3.9 mmol, 1.5 eq.) in DMF (7 mL) was added K2CO3 (1.08 g, 7.8 mmol, 3 eq.). The mixture was stirred vigorously overnight at 60° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica using ethyl acetate:hexanes eluant to provide 730 mg of 8. Yield 73%. MS m/z 400 [M+H]+

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with NaH2PO4 buffer (pH 5, 1M) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-605544d7bec5495888639f8cef03b0d1
出典データセット
uspto-grants-2014_04
特許番号
US08703700B2

反応ノート

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