Potassium Phosphate, Tribasic → (3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

HRID 711225ノート

反応式

HRID 711225 の反応式
[CH3:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][C:13]=1[F:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:13]1[CH:14]=[C:15]([CH2:18][NH2:19])[CH:16]=[CH:17][C:12]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2757541(4-Chloro-3-fluorophenyl)methanamineHCID 41926642-Methylpyridine-4-boronic acid

生成物 1

HCID 67208674(3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
96 °C

実験手順

A mixture of (2-methylpyridin-4-yl)boronic acid 15-1 (822 mg, 6.2 mmol), (4-chloro-3-fluorophenyl)methanamine 15-2 (798 mg, 5.00 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol) and K3PO4 (1.59 g, 7.50 mmol) in dioxane (10 mL) and water (1 mL) was stirred at 96° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite, washed with ethyl acetate, and dried with Na2SO4. The filtrate was concentrated by rotavap and the residue subjected to silica gel column chromatography with 6% ammonia-saturated methanol in dichloromethane as eluent to give (3-fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine 15-3 as an oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. concentrationThe filtrate was concentrated by rotavap

出典と根拠

ORDレコード
ord-002187d7f03e4e508b10ceadff063090
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

反応ノート

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