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

HRID 711236노트

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HRID 711236 반응식
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

참가 물질

7

반응물 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

생성물 1

HCID 68080154(4-(2-(Trifluoromethyl)pyridin-4-yl)phenyl)methanamine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
96 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58104957f5d54efe9fda6f9ae46f75e1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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