Boron tribromide → 2-(6-Fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol

HRID 501055노트

반응식

HRID 501055 반응식
[F:1][C:2]1[C:7]([NH:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:13]=3[CH:14]=2)[N:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[N:3]=[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:13]=3[CH:14]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH3:9]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59424801[2-Fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-yl]-methyl-amine

생성물 1

HCID 250149342-(6-Fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol수율 74.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of [2-fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-yl]-methyl-amine (31 mg, 0.114 mmol) in dichloromethane (3 mL) at 0° C. under nitrogen atmosphere, BBr3 (1M solution in CH2Cl2, 0.568 mL, 0.568 mmol) was added dropwise. The reaction mixture was stirred for 1.5 hours at room temperature. The mixture was then cooled to 0° C., saturated sodium bicarbonate solution was added (5 mL) and the resulting mixture was extracted with dichloromethane (50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification of the crude product by flash chromatography using 30% ethyl acetate in hexane afforded the title compound 2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol (22 mg) as an off-white solid. 1H NMR (400 MHz, METHANOL-d4) δ: 7.62 (d, J=7.90 Hz, 1H), 7.28 (d, J=8.78 Hz, 1H), 7.08 (dd, J=10.54, 8.20 Hz, 1H), 6.97 (s, 1H), 6.92 (d, J=2.34 Hz, 1H), 6.74 (dd, J=8.78, 2.34 Hz, 1H), 2.87 (s, 3H). ESMS: m/z 259.47 [M+1]+

후처리

  1. temperatureThe mixture was then cooled to 0° C.
  2. extractionthe resulting mixture was extracted with dichloromethane (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the crude product by flash chromatography

출처 및 근거

ORD 기록
ord-70e3c5e4564c419c926405e19fc73faf
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772256B2

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