Potassium Phosphate, Tribasic → HCID 59375395, 화합물

HRID 2193028노트

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HRID 2193028 반응식
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]

참가 물질

8

반응물 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

생성물 1

HCID 59375395HCID 59375395, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-320396cf77ba4409b270ba2aea83ec78
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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