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

HRID 501055ノート

反応式

HRID 501055 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-70e3c5e4564c419c926405e19fc73faf
出典データセット
uspto-grants-2010_08
特許番号
US07772256B2

反応ノート

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