Methanol → HCID 54509567, 화합물

HRID 2209464

반응식

HRID 2209464 반응식
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1Br.[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].CO.C([O-])([O-])=O.[Na+].[Na+]>[Al].C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=1

참가 물질

9

반응물 4

HCID 887MethanolHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 218656452-bromo-4-(4-pyridinylmethyl)Benzenamine

생성물 1

HCID 54509567HCID 54509567, 화합물수율 85.3%

시약·촉매·용매 4

HCID 241Benzene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매HCID 5359268Aluminum용매

실험 절차

4-(4-Amino-3-bromobenzyl)pyridine (1.0 gm), 3-nitrobenzene boronic acid (0.63 gm), palladium tetrakis triphenylphosphine (0.47 gm), methanol (6.5 mL), 2.0M Na2CO3 (1.9 mL) and benzene (32 mL) are combined in a reaction flask that is wrapped in aluminum foil (to prevent exposure of the reagents to light). The reaction mixture is heated to reflux for 6 hours. The progress of the reaction is monitored by thin-layer chromatography (9:1 hexane:ethyl acetate). When the starting material is converted, the reaction mixture is allowed to cool and the solvents are removed. Ethyl acetate is added to the residue, the resultant solution is filtered through a pad of Na2SO4, and concentrated. The product is isolated by preparative thin-layer chromatography (9:1 hexane:ethyl acetate) yielding 983 mg of 4-[4-amino-3-(3-nitrophenyl)benzyl]pyridine as an orange oil.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 6 hours
  3. temperatureto cool
  4. customthe solvents are removed
  5. additionEthyl acetate is added to the residue
  6. filtrationthe resultant solution is filtered through a pad of Na2SO4
  7. concentrationconcentrated
  8. customThe product is isolated by preparative thin-layer chromatography (9:1 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-81a3102cb48e4c0b8237898f90eb372f
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455252

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