Toluene → 5-Phenylpyridin-3-amine

HRID 250027노트

반응식

HRID 250027 반응식
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]1(C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(B(O)O)C=CC=CC=1>C(O)C.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>[C:9]1([C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 8176813-Amino-5-bromopyridine

생성물 1

HCID 27629015-Phenylpyridin-3-amine수율 13%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5-bromopyridin-3-amine (248 mg, 1.43 mmol), Pd(PPh3)4 (50.4 mg, 0.04 mmol), toluene (3 mL), sodium carbonate (2 M, 3 mL, 6 mmol), and phenylboronic acid (195 mg, 1.60 mmol) dissolved in ethanol (3 mL) was heated for 4 hours in an oil bath at 90° C. and allowed to cool to room temperature for 16 hours. The reaction mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The aqueous phase was washed once more with ethyl acetate, and the combined organic phases were washed with brine and dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (80% ethyl acetate/hexanes) to afford 5-phenylpyridin-3-amine (31.9 mg, 0.19 mmol, 13% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 8.17-8.42 (m, 1 H), 8.02-8.20 (m, 1 H), 7.32-7.62 (m, 4 H), 7.25 (s, 1 H), 7.06-7.20 (m, 1 H). MS (LC/MS) R.T.=0.91; [M+H]+=171.09.

후처리

  1. temperatureto cool to room temperature for 16 hours
  2. customThe reaction mixture was transferred to a separatory funnel
  3. custompartitioned between ethyl acetate and water
  4. washThe aqueous phase was washed once more with ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (80% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-a9be48c05ed444b28a910dcd8b2a6fbe
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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