Dichloromethane → HCID 86650643, 화합물

HRID 1623399노트

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HRID 1623399 반응식
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22](B(O)O)[C:21]([O:27][CH3:28])=[CH:20][N:19]=1.C(Cl)Cl>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[N:7]=2)[C:21]([O:27][CH3:28])=[CH:20][N:19]=1

참가 물질

7

반응물 3

HCID 6344DichloromethaneHCID 46738707B-(2-Chloro-5-methoxy-4-pyridinyl)boronic acidHCID 581273766-bromo-N-(3-fluorobenzyl)pyridin-2-amine

생성물 1

HCID 86650643HCID 86650643, 화합물수율 7.8%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

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온도
110 °C

실험 절차

To a solution of 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine (555 mg, 1.974 mmol) and 2-chloro-5-methoxypyridin-4-ylboronic acid (518 mg, 2.76 mmol) in DME (4 ml) and 2M Na2CO3 aq (2 ml) was added PdCl2(dppf).CH2Cl2 adduct (81 mg, 0.099 mmol). This was then heated at 110° C. for 5 h. The reaction mixture was allowed to cool and then the DME was evaporated under reduced pressure. The resulting residue was partitioned between EtOAc and water. The organics were combined, then washed with H2O (×3), saturated aq. brine (×3), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel; 15% to 25% EtOAc/hexane) to give 2′-chloro-N-(3-fluorobenzyl)-5′-methoxy-2,4′-bipyridin-6-amine (53 mg).

후처리

  1. temperatureto cool
  2. customthe DME was evaporated under reduced pressure
  3. customThe resulting residue was partitioned between EtOAc and water
  4. washwashed with H2O (×3), saturated aq. brine (×3)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography (silica gel; 15% to 25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-48c994532d3d48eda44610a2ab68197a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778951B2

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