Methanol → HCID 54509567、化合物

HRID 2209464

反応式

HRID 2209464 の反応式
[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

参加物

9

反応物 4

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

生成物 1

HCID 54509567HCID 54509567、化合物収率 85.3%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒HCID 5359268Aluminum溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-81a3102cb48e4c0b8237898f90eb372f
出典データセット
uspto-grants-1995_10
特許番号
US05455252

関連ノート

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