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Hydrochloric Acid → Methyl 4-(4-amino-6-methoxyquinolin-2-yl)benzoate

HRID 55825
ノート
印刷プレビュー

反応式

HRID 55825 の反応式
ClC1C=C(C=CC=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16](O)[CH:17]=2)[N:12]=1)C(O)=O.[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].[C:35]([O-:38])([O-])=O.[K+].[K+].Cl.C[N:43](C=O)C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:43][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:38][CH3:35])[CH:17]=2)[N:12]=[C:11]([C:29]2[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=2)[CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 56960912Cavosonstat

生成物 1

HCID 66980112Methyl 4-(4-amino-6-methoxyquinolin-2-yl)benzoate収率 46%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

実験手順

A mixture solution of Intermediate 8 (4.70 g, 22.5 mmol), 4-methoxycarbonylphenylboronic acid (4.01 g, 22.5 mmol), K2CO3 (6.53 g, 47.2 mmol), Pd(dppf)Cl2 (470 mg, 0.407 mmol) in DMF (20 mL) and H2O (4 mL) was stirred under N2 atmosphere at 130° C. for 5 hours. The mixture was cooled, acidified with aqueous HCl (1M) until pH=6 and extracted with EtOAc (80 mL×3). The combined organic layers were washed with brine (150 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was washed with EtOAc (50 mL), the mixture was filtered then concentrated to give the product (3.20 g, yield 46%) as an off-white solid.

後処理

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (80 mL×3)
  3. washThe combined organic layers were washed with brine (150 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with EtOAc (50 mL)
  7. filtrationthe mixture was filtered
  8. concentrationthen concentrated

出典と根拠

ORDレコード
ord-cc115375d5d94fefb8a755343c3e4afc
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09433618B2

反応ノート

読み込み中…

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