Boron tribromide → 2-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol

HRID 1802274ノート

反応式

HRID 1802274 の反応式
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][N:11]2[N:10]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[OH:2])[N:18]=[C:12]2[CH:13]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 677742602-(2-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

生成物 1

HCID 1363723582-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (2.3 g, 9.6 mmol) (Example 102, step c) in DCM (60 ml) was added a solution of BBr3 (1 M in DCM, 28.7 ml, 28.7 mmol). The mixture was allowed to warm up to 25° C. and stirring was continued for 2 h. Volatiles were removed under reduced pressure and the crude residue was extracted with DCM and washed with aq. NaHCO3 solution. The organic layer was washed with brine, dried over Na2SO4 and concentrated to get the crude product which was washed with 10% DCM in hexane to afford the title compound as off-white solid (1.3 g, 60%). LC-MS: m/z=227.4 [M+H]+.

後処理

  1. customVolatiles were removed under reduced pressure
  2. extractionthe crude residue was extracted with DCM
  3. washwashed with aq. NaHCO3 solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto get the crude product which
  8. washwas washed with 10% DCM in hexane

出典と根拠

ORDレコード
ord-89327fe6c6de412b9fb37259b93d66bf
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

反応ノート

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