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

HRID 55825
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HRID 55825 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc115375d5d94fefb8a755343c3e4afc
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09433618B2

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