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

HRID 854886ノート

反応式

HRID 854886 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5bc26005c1b4475992ea3105f6e94e4f
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

反応ノート

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