Potassium Carbonate → HCID 70206537, 화합물

HRID 2367924노트

반응식

HRID 2367924 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 70206537HCID 70206537, 화합물수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-605544d7bec5495888639f8cef03b0d1
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703700B2

반응 노트

불러오는 중…