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

HRID 2423401ノート

反応式

HRID 2423401 の反応式
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

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 53419781Methyl 7-bromoquinoline-4-carboxylate

生成物 1

HCID 136146134Methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate収率 55%

試薬・触媒・溶媒 3

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

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-e73e2523f1cd4f8f86d67b0637673ba0
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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