Water → 2,6-Difluoro-3-[5-(3-hydroxy-phenyl)-benzothiazol-2-ylmethoxy]-benzamide

HRID 538518ノート

反応式

HRID 538518 の反応式
[F:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[CH:23]=4)=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=[C:7]([F:30])[C:3]=1[C:4]([NH2:6])=[O:5].B(Br)(Br)Br.O>C(Cl)Cl>[F:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=4)=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=[C:7]([F:30])[C:3]=1[C:4]([NH2:6])=[O:5]

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 594028792,6-Difluoro-3-[5-(3-methoxy-phenyl)-benzothiazol-2-ylmethoxy]-benzamide

生成物 1

HCID 594028872,6-Difluoro-3-[5-(3-hydroxy-phenyl)-benzothiazol-2-ylmethoxy]-benzamide収率 16.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a suspension of 2,6-difluoro-3-[5-(3-methoxy-phenyl)-benzothiazol-2-ylmethoxy]-benzamide (0.14 g, 0.3 mmol) in 15 ml of anhydrous DCM was added drop wise boron tribromide (0.493 g, 1.9 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 3 h under nitrogen atmosphere. To the reaction mixture 5 ml of water was added at 0° C. The compound was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The compound was purified by column chromatography on silica (230-400μ) using ethyl acetate (40:60) as the eluent to provide the title compound as yellow solid (0.020 g, 14%). 1H NMR (DMSO-d6, 400 MHz): δ 5.71 (s, 2H), 6.80 (dd, 1H, J=9.6 Hz (o-coupling), 7.11 (dt, 1H, J=8.0 Hz (o-coupling), 7.17 (dt, 1H, J=8.0 Hz (o-coupling), 7.29 (t, 1H, J=8.0 Hz (o-coupling), 7.39-7.43 (m, 1H), 7.71 (dd, 1H, J=9.6 Hz) 7.89 (broad s, 1H), 8.18-8.22 (m, 2H). MS ES+ (413.01), HPLC (method 5) Rt=14.95 min

後処理

  1. extractionThe compound was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated to dryness under reduced pressure
  4. customThe compound was purified by column chromatography on silica (230-400μ)

出典と根拠

ORDレコード
ord-dfc795933f174322b37670ebb5cd7345
出典データセット
uspto-grants-2014_10
特許番号
US08865736B2

反応ノート

読み込み中…