Water → HCID 136146135, 화합물

HRID 2423397노트

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HRID 2423397 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=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:34][C:31]1[CH:32]=[CH:33][C:28]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[N:9]3)=[CH:4][CH:3]=2)=[CH:29][CH:30]=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 67245888Dimethyl 7-bromoquinoline-2,4-dicarboxylate

생성물 1

HCID 136146135HCID 136146135, 화합물수율 51%

시약·촉매·용매 3

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

실험 절차

A mixture of 150 mg (0.46 mmol) of dimethyl 7-bromo-2,4-quinolinedicarboxylate synthesized according the procedure of Corey, E. J. and Tramontano, A., 1981 J. Am. Chem. Soc. 103:5599-5600 and Carrigan, C. N., et al, 1999 Bioorg. Med. Chem. Lett. 9:2607-2612, 153 mg (0.69 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 5 mg (0.02 mmol) of palladium acetate, 12 mg (0.05 mmol) of triphenylphosphine, 345 mg (1.62 mmol) of K3PO4, and 40 μL (2.31 mmol) of H2O in 3 mL of dioxane were stirred at 60° C. for 1.5 hr. EtOAc was then added and the solution washed with H2O. The aqueous layer was extracted with EtOAc and then the combined organics were washed with brine and concentrated. A small amount of cold EtOAc was added to the residue and the solids were collected by suction filtration, washed with cold EtOAc then dried to yield 79 mg (51%) of dimethyl 7-(4-hydroxyphenyl)-2,4-quinolinedicarboxylate as a brown solid. 1H NMR (400 MHz, CDCl3): δ 9.79 (s, 1H), 8.72 (d, J=9 Hz, 1H), 8.41-8.38 (m, 2H), 8.17 (d, J=9 Hz, 1H), 7.77 (d, J=8 Hz, 2H), 6.91 (d, J=8 Hz, 2H), 4.00 (s, 3H), 3.97 (s, 3H). ESI-LCMS m/z 338 (M+H)+.

후처리

  1. customsynthesized
  2. washthe solution washed with H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. concentrationconcentrated
  6. additionA small amount of cold EtOAc was added to the residue
  7. filtrationthe solids were collected by suction filtration
  8. washwashed with cold EtOAc
  9. customthen dried

출처 및 근거

ORD 기록
ord-1eabd97b8e694b49b19102313482f6aa
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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