Potassium Carbonate → HCID 22329144、化合物

HRID 586896ノート

反応式

HRID 586896 の反応式
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH3:14])=[C:5]([F:15])[CH:4]=1.Br[C:19]1[CH:20]=[CH:21][C:22]2[N:28]([CH:29]=[O:30])[CH2:27][CH2:26][C:25]([C:31]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][N:41]([CH3:48])[CH:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:36][CH:35]=3)=[O:32])=[CH:24][C:23]=2[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.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>[CH3:14][CH2:13][O:12][CH2:11][CH2:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:19]2[CH:20]=[CH:21][C:22]3[N:28]([CH:29]=[O:30])[CH2:27][CH2:26][C:25]([C:31]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([CH2:40][N:41]([CH3:48])[CH:42]5[CH2:47][CH2:46][O:45][CH2:44][CH2:43]5)=[CH:38][CH:39]=4)=[O:32])=[CH:24][C:23]=3[CH:49]=2)=[CH:4][C:5]=1[F:15]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 22329057HCID 22329057、化合物HCID 867567934-(2-Ethoxyethoxy)-3-fluorophenyl borate

生成物 1

HCID 22329144HCID 22329144、化合物収率 76.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

実験手順

In a mixture of water:ethanol:toluene (1:1:10, v/v, 18.0 ml) were dissolved 4-[(2-ethoxy)ethoxy]-3-fluorophenyl borate (355 mg) and 7-bromo-1-formyl-N-(4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (517 mg). To the solution was added potassium carbonate (344 mg), and the mixture was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (48 mg), and the mixture was heated to reflux under argon atmosphere for 10 hours. The mixture was diluted with ethyl acetate, and washed with water and saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (30 g, ethyl acetate→ethyl acetate:ethanol=10:1→ethyl acetate:ethanol:triethylamine=100:10 :1) and recrystallized from ethanol to give 7-[4-(2-ethoxy)ethoxy-3-fluorophenyl]-1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 20) (476 mg, 76%) as white crystals.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux under argon atmosphere for 10 hours
  3. washwashed with water and saturated brine
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (30 g, ethyl acetate→ethyl acetate:ethanol=10:1→ethyl acetate:ethanol:triethylamine=100:10 :1)
  7. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-132e596cc6604389935ce20f24067382
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

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