3-Bromo-4-chloropyridine → HCID 66835317, 화합물

HRID 61912

반응식

HRID 61912 반응식
[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

참가 물질

8

반응물 4

HCID 8176963-Bromo-4-chloropyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2회HCID 23676156Sodium t-butoxide

생성물 1

HCID 66835317HCID 66835317, 화합물수율 4%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0582a6c2a42b43f8a3e683f3bc3d7248
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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