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

HRID 2194924ノート

反応式

HRID 2194924 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bea63c37d3aa47668e28e54b05e7c7be
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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