Potassium Phosphate, Tribasic → HCID 59375395、化合物

HRID 2193028ノート

反応式

HRID 2193028 の反応式
FC(F)(F)S(O[C:7]1[C:16]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=2[C:14]2[C:9](=[CH:10][CH:11]=[N:12][C:13]=2[O:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:8]=1)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:37]1(P(C2CCCCC2)C2CCCCC2)[CH2:42]CCC[CH2:38]1.C(B1OC(C)(C)C(C)(C)O1)(C)=C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:23]([O:22][C:13]1[N:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:7]([C:37]([CH3:42])=[CH2:38])=[N:8]2)[CH2:24][CH2:25][CH3:26]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 593755261-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate

生成物 1

HCID 59375395HCID 59375395、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate (1.00 g, 2.39 mmol), potassium phosphate tribasic (1.52 g, 7.17 mmol), palladium(II) acetate (0.0540 g, 0.239 mmol), and tricyclohexylphosphine (0.134 g, 0.478 mmol) were combined in pressure vessel. Toluene (20 ml), water (6.67 ml), and isopropenylboronic acid pinacol ester (0.899 ml, 4.78 mmol) were added. The resulting suspension was purged with argon (subsurface bubbling) for 10 min. The reaction mixture was stirred in a sealed pressure vessel at 100° C. for 2.5 h. After cooling the reaction mixture was diluted with EtOAc, and washed with aqueous ammonium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated to a crude residue that was adsorbed on to silica gel and purified by column chromatography on silica gel eluting with an EtOAc/hexane gradient to afford 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine. LRMS (ESI) calc'd for (C19H19FN2O) [M+H]+, 311.1; found 311.1.

後処理

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
  2. temperatureAfter cooling the reaction mixture
  3. additionwas diluted with EtOAc
  4. washwashed with aqueous ammonium chloride
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude residue that
  8. custompurified by column chromatography on silica gel eluting with an EtOAc/hexane gradient

出典と根拠

ORDレコード
ord-320396cf77ba4409b270ba2aea83ec78
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

読み込み中…