Potassium Phosphate, Tribasic → HCID 24822773、化合物

HRID 1925301ノート

反応式

HRID 1925301 の反応式
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

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 54638006-Hydroxy-1-naphthoic acidHCID 11481892HCID 11481892、化合物HCID 67346612HCID 67346612、化合物

生成物 1

HCID 24822773HCID 24822773、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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))

出典と根拠

ORDレコード
ord-76a66a69a6e441e395e1e3ee8826a1a1
出典データセット
uspto-grants-2012_05
特許番号
US08178557B2

反応ノート

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