Potassium Carbonate → 1,4-Bis(5-phenyl-2-pyridyl)hexahydro-1,4-diazepine

HRID 460374ノート

反応式

HRID 460374 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>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>[C:22]1([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[CH:20]=[CH:19][C:18]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

生成物 1

HCID 102013941,4-Bis(5-phenyl-2-pyridyl)hexahydro-1,4-diazepine

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

Under nitrogen, to a solution of the 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (200 mg, 0.585 mmol) synthesized in Reference Example 1 in ethanol-toluene (2.0 mL-2.0 mL) were added phenylboronic acid (130.0 mg, 1.07 mmol), tetrakis(triphenylphosphine)palladium (56.0 mg, 0.050 mmol) and a 2.0 M aqueous potassium carbonate (0.5 mL, 1.0 mmol), and the resulting mixture was stirred at 80° C. for 3 hours. After cooling, the organic layer was collected and the aqueous layer was extracted with chloroform. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield crude crystals. The crude crystals were recrystallized from chloroform-hexane to yield the title compound as slightly yellow needles (melting point: 221.0–222.0° C.) (61.0 mg, yield: 31%).

後処理

  1. temperatureAfter cooling
  2. customthe organic layer was collected
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. customto yield crude crystals
  8. customThe crude crystals were recrystallized from chloroform-hexane

出典と根拠

ORDレコード
ord-a0d5d1cef3eb4e1392a20d9dbe14e547
出典データセット
uspto-grants-2007_03
特許番号
US07196101B2

反応ノート

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