3-Bromo-4-chloropyridine → HCID 66835317、化合物

HRID 61912

反応式

HRID 61912 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1Cl.CC(C)([O-])C.[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:21]4[CH:20]=[N:19][CH:18]=[CH:17][C:22]=4[O:15][C:9]=3[C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

参加物

8

反応物 4

HCID 8176963-Bromo-4-chloropyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2 回HCID 23676156Sodium t-butoxide

生成物 1

HCID 66835317HCID 66835317、化合物収率 4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 2.5 g), 3-bromo-4-chloro-pyridine (2 g), sodium t-butoxide (3 g), Pd2dba3 (476 mg), and S-Phos (512 mg), toluene (20 ml) was added, and the mixture was stirred and heated at 100° C. overnight under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and filtered through Celite. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine. Thereafter, the organic layer was dried over sodium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (112 mg, 4%).

後処理

  1. temperatureAfter cooling
  2. filtrationfiltered through Celite
  3. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  4. dry with materialThereafter, the organic layer was dried over sodium sulfate
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0582a6c2a42b43f8a3e683f3bc3d7248
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

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