Potassium Phosphate, Tribasic → HCID 24822773, 화합물

HRID 1925301노트

반응식

HRID 1925301 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:16].[OH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([C:28]([OH:30])=[O:29])=[CH:23][CH:22]=[CH:21]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C(CCC)=CC(CCC)=CC=1CCC)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[F:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[O:17][C:18]1[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=1)[C:24]([C:28]([OH:30])=[O:29])=[CH:23][CH:22]=[CH:21]3)=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 54638006-Hydroxy-1-naphthoic acidHCID 11481892HCID 11481892, 화합물HCID 67346612HCID 67346612, 화합물

생성물 1

HCID 24822773HCID 24822773, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A resealable tube was charged with 4-chloro-3-fluoro-6,7-dimethoxyquinoline (prepared by the method described in WO 98/13350) (0.610 g, 2.52 mmol), 6-hydroxy-1-naphthoic acid (0.474 g, 2.52 mmol), palladium acetate (0.023 g, 0.101 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (0.086 g, 0.202 mmol), potassium phosphate (2.14 g, 10.08 mmol), and DMF (12.6 mL, Aldrich). The system was flushed with argon and the tube was sealed. The mixture was stirred at 100° C. for 19 h then cooled to RT. Water (13 mL) was added, and the pH was adjusted to 6-7 with aqueous 6 N HCl solution. The resulting precipitate was filtered, washed with water, and purified by column chromatography on silica gel (eluting with 0-100% (50:50:2, EtOAc:hexane:AcOH)) to afford 6-(3-fluoro-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid as an off-white solid. MS (ESI, pos. ion) m/z: 394.0 (M+H). Mass Calc'd for C22H16FNO5: 393.1

후처리

  1. customprepared by the method
  2. customThe system was flushed with argon
  3. customthe tube was sealed
  4. temperaturethen cooled to RT
  5. additionWater (13 mL) was added
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water
  8. custompurified by column chromatography on silica gel (eluting with 0-100% (50:50:2, EtOAc:hexane:AcOH))

출처 및 근거

ORD 기록
ord-76a66a69a6e441e395e1e3ee8826a1a1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178557B2

반응 노트

불러오는 중…