Potassium Phosphate, Tribasic → (4-(2-(Trifluoromethyl)pyridin-4-yl)phenyl)methanamine

HRID 711236ノート

反応式

HRID 711236 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.Cl.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=2)O1.[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:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=2)[CH:7]=[CH:6][N:5]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 147614424-Chloro-2-(trifluoromethyl)pyridineHCID 164270881-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochloride

生成物 1

HCID 68080154(4-(2-(Trifluoromethyl)pyridin-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 4-chloro-2-(trifluoromethyl)pyridine 28-1 (54 mg, 0.3 mmol), (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochloride 28-2 (81 mg, 0.3 mmol), Pd(PPh3)4 (35 mg, 0.03 mmol) and K3PO4 (212 mg, 1.0 mmol) in dioxane (1.6 mL) and water (0.2 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 the filtrate was redistributed between ethyl acetate and water. The organic phase was dried over Na2SO4 and concentrated with rotavap. The residue was subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (4-(2-(trifluoromethyl)pyridin-4-yl)phenyl)methanamine 28-3 as an oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite (washed with ethyl acetate)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated with rotavap

出典と根拠

ORDレコード
ord-58104957f5d54efe9fda6f9ae46f75e1
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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