Potassium Carbonate → HCID 44480908、化合物

HRID 1521575ノート

反応式

HRID 1521575 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=3[CH:13]=2)[CH:15]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 149781117-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

生成物 1

HCID 44480908HCID 44480908、化合物

試薬・触媒・溶媒 1

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒

反応条件

温度
100 °C

実験手順

A sealable tube containing the title compound from Example 2 Step C (0.300 g, 1.25 mmol), 3-pyridylboronic acid (0.200 g, 1.62 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.018 g, 0.025 mmol) and potassium carbonate (0.368 g, 3.75 mmol) was flushed with nitrogen before tort-butanol (14.0 mL) and water (1.6 mL) were added. It was flushed again with nitrogen, sealed tightly and heated to 100° C. overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-12% methanol in ethyl acetate) provided the title compound: LCMS m/z 239.09 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.72 (s, 1H), 8.46 (d, J=4.2 Hz, 1H), 7.86 (ddd, J=1.8, 1.9, 8.0 Hz, 1H), 7.41-7.39 (m, 2H), 7.35 (dd, J=4.8, 7.9 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 2.81 (t, J=7.2 Hz, 2H), 2.35-2.31 (m, 2H), 2.26-2.20 (m, 2H).

後処理

  1. customwas flushed with nitrogen before tort-butanol (14.0 mL) and water (1.6 mL)
  2. additionwere added
  3. customIt was flushed again with nitrogen
  4. customsealed tightly
  5. temperatureThe reaction was then cooled to room temperature
  6. additionpoured into saturated aqueous sodium chloride solution
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by flash chromatography on silica gel (0-12% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-273846544b8345d9a46c240baef56feb
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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