Triethylamine → 4'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile

HRID 5680

반응식

HRID 5680 반응식
C(N(CC)CC)C.Cl.[CH2:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:10].Br[C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[C:35]#[N:36]>C(O)CCC.O.[Pd](Cl)Cl>[CH2:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:33]3[C:34]([C:35]#[N:36])=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:10]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 162722-BromobenzonitrileHCID 677828274-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride

생성물 1

HCID 150208494'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile수율 91.1%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 2631-Butanol용매HCID 962Water용매

실험 절차

Triethylamine (13.8 ml) was added to a mixture of 4-[(2-ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (12.74 g), 2-bromobenzonitrile (5.92 g) and palladium chloride (0.13 g) in butanol (80 ml) and water (40 ml) and the mixture was heated at reflux for 3 hours. The hot reaction mixture was filtered through diatomaceous earth and the filtrate was stirred while allowing to cool to ambient temperature. The mixture was then cooled to 4° C. for 30 minutes. The solid which crystallised was collected by filtration, washed with cold butanol (16 ml) and water (2×16 ml) and then dried at 55° C. to give 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile (10.8 g); m.p. 161°-162° C.; NMR (CDCl3): 1.4(t,3H), 2.97(q,2H), 5.35(s,2H), 6.76(s,1H), 7.4-7.6(m,3H), 7.6-7.8(m,6H), 8.0(d,1 H), 8.25(d,1H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe hot reaction mixture was filtered through diatomaceous earth
  4. temperatureThe mixture was then cooled to 4° C. for 30 minutes
  5. customThe solid which crystallised
  6. filtrationwas collected by filtration
  7. washwashed with cold butanol (16 ml) and water (2×16 ml)
  8. customdried at 55° C.

출처 및 근거

ORD 기록
ord-19b3524e42254cd798a618b4d5e376b5
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245035

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