Potassium Carbonate → ethyl 7-(2-furyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854886노트

반응식

HRID 854886 반응식
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 69517680ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 69518409ethyl 7-(2-furyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate수율 21%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

The ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 9a, Step 2 (2.0 g, 5.02 mmol), 2-furylboronic acid (0.62 g, 5.52 mmol), K2CO3 (2.08 g, 15.06 mmol), and PdCl2(PPh3)2 (106 mg, 0.15 mmol) were mixed in dioxane (20 mL) in a sterling bomb. Carbon monoxide was bubbling to 40 psi. The reaction was heated to 80° C. for 12 h. After filtration, the reaction was quenched with NH4Cl and extracted with EtOAc. The organic layer was washed and dried over MgSO4. The filtrate was evaporated and dried in vacuo to afford crude which was purified Biotage Chromatography with 10 to 20% ethyl acetate in hexane to give yellow solid (350 mg, 21%): LCMS m/z 339.05 (M+H). 1H NMR (CDCl3/300 MHz) 7.74 (s, 1H), 7.51 (s, 1H), 8.97 (m, 3H), 6.76 (d, 1H, J=3.3 Hz), 6.51 (m, 1H), 5.73 (q, 1H, J=6.9 Hz), 4.34 (m,2H), 1.36 (t, 3H, J=7.2 Hz).

후처리

  1. customCarbon monoxide was bubbling to 40 psi
  2. filtrationAfter filtration
  3. customthe reaction was quenched with NH4Cl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed
  6. dry with materialdried over MgSO4
  7. customThe filtrate was evaporated
  8. customdried in vacuo
  9. customto afford crude which
  10. customwas purified Biotage Chromatography with 10 to 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-5bc26005c1b4475992ea3105f6e94e4f
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

반응 노트

불러오는 중…