Sodium Carbonate → [2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]acetonitrile

HRID 2194924노트

반응식

HRID 2194924 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.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]>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 184142962-(4-Bromo-2-methylphenyl)acetonitrileHCID 58083347[2-(3-Methoxypropyl)phenyl]boronic acid

생성물 1

HCID 58083338[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]acetonitrile

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (4-bromo-2-methylphenyl)acetonitrile (1 eq.) and [2-(3-methoxypropyl)phenyl]boronic acid from EXAMPLE 3 step 1, in DMF (0.22M) was added aqueous Na2CO3 (2M; 3 eq.). Nitrogen was bubbled in the solution for 15 min before the addition of PdCl2(dppf)2 (0.05 eq.). The final mixture was stirred at 90° C. for 12 h, cooled to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, HCl (0.01M), brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (5 to 30% in 30 min) afforded the desired compound as a colorless oil.

후처리

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with water, HCl (0.01M), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  8. washeluting with Hex/EtOAc (5 to 30% in 30 min)

출처 및 근거

ORD 기록
ord-bea63c37d3aa47668e28e54b05e7c7be
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

반응 노트

불러오는 중…