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

HRID 711225노트

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HRID 711225 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 67208674(3-Fluoro-4-(2-methylpyridin-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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-002187d7f03e4e508b10ceadff063090
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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