Carbon Dioxide → Trifluoromethanesulfonic acid 7-benzyloxy-6-methoxy-quinolin-4-yl ester

HRID 445470ノート

反応式

HRID 445470 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.C(=O)=O.[F:33][C:34]([F:40])([F:39])[S:35](Cl)(=[O:37])=[O:36]>CN(C)C1C=CN=CC=1.O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][S:35]([C:34]([F:40])([F:39])[F:33])(=[O:37])=[O:36])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 79372,6-LutidineHCID 79000Trifluoromethanesulfonyl chlorideHCID 178486758HCID 178486758、化合物

生成物 1

HCID 57810077Trifluoromethanesulfonic acid 7-benzyloxy-6-methoxy-quinolin-4-yl ester収率 83.8%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a dry 2 L RBF containing 7-benzyloxy-6-methoxyquinolin-4-ol (75.3 g, 267 mmol) was added DCM (1 L), 4-dimethylaminopyridine (3.28 g, 26.8 mmol) and 2,6-lutidine (62 mL, 534 mmol). The mixture was cooled to −20° C. by controlled addition of dry ice to an acetone bath. Trifluoromethanesulfonyl chloride (37 mL, 350 mmol) was added dropwise to the cooled solution with magnetic stirring over 25 minutes. After addition was complete, the mixture was stirred in bath for 20 minutes, then at room temperature for 3 hours. LCMS indicated reaction completion. The reaction mixture was concentrated in vacuo and placed under high vacuum to remove residual 2,6-lutidine. To the resulting brown solids was added methanol (3.5 L). The resulting slurry was stirred with mechanical stirrer for 30 min before adding water (1.5 L). The solids were isolated by filtration, followed by a water wash. The resulting solid was dried under high vacuum overnight yielding trifluoromethanesulfonic acid 7-benzyloxy-6-methoxy-quinolin-4-yl ester as a light brown solid (92.2 g, 83.8%). 1H NMR (400 MHz, DMSO, d6): δ 8.82 (d, 1H), 7.67 (s, 1H), 7.59 (d, 1H), 7.54-7.52 (m, 2H), 7.46-7.42 (m, 2H), 7.39-7.36 (m, 1H), 7.23 (s, 1H), 5.35 (s, 2H), 3.97 (s, 3H). LC/MS: M+H=414.

後処理

  1. additionAfter addition
  2. stirringthe mixture was stirred in bath for 20 minutes
  3. waitat room temperature for 3 hours
  4. customreaction completion
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customto remove residual 2,6-lutidine
  7. additionTo the resulting brown solids was added methanol (3.5 L)
  8. stirringThe resulting slurry was stirred with mechanical stirrer for 30 min
  9. additionbefore adding water (1.5 L)
  10. customThe solids were isolated by filtration
  11. washwash
  12. customThe resulting solid was dried under high vacuum overnight

出典と根拠

ORDレコード
ord-fcd3b1acbc6e4165ad54929d2422dc62
出典データセット
uspto-grants-2013_07
特許番号
US08476298B2

反応ノート

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