Boron tribromide → 2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol

HRID 2241808ノート

反応式

HRID 2241808 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]([CH3:19])[CH3:18])=[N:15][CH:16]=3)=[N:8][C:7]=2[CH:20]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[CH3:18][N:17]([CH3:19])[C:14]1[N:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:20][C:7]=3[N:8]=2)=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 247806565-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine

生成物 1

HCID 247806572-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol収率 23.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

To a solution of 5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (0.368 mmol) in dichloromethane (2.0 mL) was added BBr3 in dichloromethane (1.84 mmol) at 0° C. under an atmosphere of argon and the reaction stirred for 1 h at 0° C. The reaction mixture was neutralized with NaHCO3 (sat. aq.) and dichloromethane was added. The layers were separated and the aqueous phase was extracted with dichloromethane (4×). The combined organic phases were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was purified by preparative HPLC to give 22.3 mg of the title compound as a white solid. 1H NMR δ ppm 9.44 (s, 1H), 8.83 (d, 1H), 8.13 (dd, 1H), 7.48 (d, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 6.76 (dd, 1H), 3.14 (s, 6H). MS m/z (M+H) 256.

後処理

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (4×)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents removed in vacuo
  7. customThe crude material was purified by preparative HPLC

出典と根拠

ORDレコード
ord-52538839318447f79a7015f49c633089
出典データセット
uspto-grants-2010_03
特許番号
US07670591B2

反応ノート

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