Triethylamine → 4-(4'-Cyano-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

HRID 381842

반응식

HRID 381842 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:15][CH:14]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoateHCID 27343264-Cyanophenylboronic acid

생성물 1

HCID 217517094-(4'-Cyano-biphenyl-4-yl)4-oxo-butyric acid, methyl ester수율 58.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
105 °C

실험 절차

A stirred mixture of (4-cyano-phenyl)boronic acid (0.220 g, 0.00150 mol), 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (0.2715 g, 0.00100 mol), triethylamine (0.418 mL, 0.0030 mol), tri(O-toluyl)phosphine (0.0191 g, 0.0000628 mol) and palladium(II)acetate (0.0067 g, 0.000030 mol) in dry dimethylformamide (4.0 mL) was heated at 105° C. under nitrogen for 2 hours and allowed to cool. For convenience, allowed to stand overnight. The mixture was diluted with diethyl ether, and the resulting suspension was filtered through Celite. The Celite and filtercake were washed with additional diethyl ether then dichloromethane. The filtrate and washings were combined and washed with 0.5 M aqueous hydrochloric acid, water, 3% aqueous ammonium hydroxide, water, and brine. The organics were dried (Na2SO4) and rotary evaporated. The residue was dissolved (chloroform) and chromatographed on silica gel (35 g, 230-400 mesh), eluting with hexanes-acetone (4:1, 30×30 mL) to give 0.172 g of 4-(4′-cyano-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid; mp 149-151° C.

후처리

  1. temperatureto cool
  2. filtrationthe resulting suspension was filtered through Celite
  3. washThe Celite and filtercake were washed with additional diethyl ether
  4. washwashed with 0.5 M aqueous hydrochloric acid, water, 3% aqueous ammonium hydroxide, water, and brine
  5. dry with materialThe organics were dried (Na2SO4) and rotary evaporated
  6. dissolutionThe residue was dissolved (chloroform)
  7. customchromatographed on silica gel (35 g, 230-400 mesh)
  8. washeluting with hexanes-acetone (4:1, 30×30 mL)

출처 및 근거

ORD 기록
ord-320f05eec1b64f479fe60781f1d2309d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307089B2

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