Water → HCID 136146135、化合物

HRID 2423397ノート

反応式

HRID 2423397 の反応式
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

参加物

9

反応物 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

生成物 1

HCID 136146135HCID 136146135、化合物収率 51%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-1eabd97b8e694b49b19102313482f6aa
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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