Potassium Carbonate → 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

HRID 2212606

反応式

HRID 2212606 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:21])=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[C:5]([CH3:23])([CH3:22])[CH2:4][C:3]1=[O:24].Br[C:26]1[C:27]([F:37])=[C:28]([CH:31]=[C:32]([F:36])[C:33]=1[O:34][CH3:35])[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:37][C:27]1[C:26]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:22])([CH3:23])[CH2:4][C:3](=[O:24])[N:2]3[CH3:1])=[CH:7][C:8]=2[CH3:21])=[C:33]([O:34][CH3:35])[C:32]([F:36])=[CH:31][C:28]=1[CH:29]=[O:30]

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 219664313-Bromo-2,5-difluoro-4-methoxybenzaldehydeHCID 21966467HCID 21966467、化合物

生成物 1

HCID 219664662,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1,4,4,6-tetramethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinoline-2-one (0.36 g, 1.1 mmol), 3-bromo-2,5-difluoro-4-methoxybenzaldehyde (example 13 a) (0.25 g, 0.1 mmol) and potassium carbonate (0.275 g, 1.99 mmol) in toluene (5 mL), ethanol (1 mL) and water (0.75 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) was added and the mixture heated at reflux under argon for 20 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (0%–20% ethyl acetate in hexane) to give 97 mg of 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde.

後処理

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 20 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (0%–20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-d2d5e6a394c041c89ee0859a93a0cc5d
出典データセット
uspto-grants-2006_09
特許番号
US07102000B2

関連ノート

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