Water → Methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate

HRID 2423401노트

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HRID 2423401 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=[N:9]3)=[CH:4][CH:3]=2)=[CH:25][CH:26]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 53419781Methyl 7-bromoquinoline-4-carboxylate

생성물 1

HCID 136146134Methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate수율 55%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

A mixture of 160 mg (0.60 mmol) of methyl 7-bromo-4-quinolinecarboxylate, 200 mg (0.90 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 7 mg (0.03 mmol) of palladium(II)acetate, 16 mg (0.06 mmol) of triphenylphosphine, 450 mg (2.10 mmol) of K3PO4 and 50 uL (3.01 mmol) of H2O in 3 mL of dioxane was stirred at 60° C. for 1.5 hr. EtOAc was added then the organics were washed with H2O and brine then concentrated. The residue was suspended in cold EtOAc and the solids were collected by suction filtration, washed with cold EtOAc and dried to give 92 mg (55%) of methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate as a tan solid. 1H NMR (400 MHz, CDCl3): δ 9.75 (s, 1H), 9.03 (s, 1H), 8.63 (d, J=9 Hz, 1H), 8.25 (d, J=2 Hz, 1H), 8.03 (dd, JA=2 Hz, JB=9 Hz, 1H), 7.87 (s, 1H), 7.72 (d, J=8 Hz, 2H), 6.90 (d, J=8 Hz, 2H), 3.98 (s, 3H). ESI-LCMS m/z 280 (M+H)+.

후처리

  1. washthe organics were washed with H2O and brine
  2. concentrationthen concentrated
  3. filtrationthe solids were collected by suction filtration
  4. washwashed with cold EtOAc
  5. customdried

출처 및 근거

ORD 기록
ord-e73e2523f1cd4f8f86d67b0637673ba0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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