Water → 5-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole

HRID 1263434ノート

反応式

HRID 1263434 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[CH:6]2.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[CH:6]2)=[N+:19]=[N-:20]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 105657815-(Bromomethyl)-1-(2-tetrahydropyranyl)indazole2 回

生成物 1

HCID 105390775-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole収率 99.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 5-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (compound 93, 3.0 g, 10.2 mmol) in DMF (30 mL), was added with sodium azide (Aldrich, 2.64 g, 40.6 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution formed. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with ether (2×150 mL). Combined organic layers were washed with brine, then dried (MgSO4). Evaporation of solvent gave the product (94) as a yellow oil (2.61 g, 99%). TLC Rf 0.63 (60:40 hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ2.03-2.15 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.02 (m, 1H), 4.52 (s, 1H), 5.71 (d, 1H, J=9.4 Hz), 7.32 (d, 1H, J=8.8 Hz), 7.56 (d, 1H, J=8.8 Hz), 7.63 (s, 1H), 8.00 (s, 1H).

後処理

  1. customa yellow solution formed
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ether (2×150 mL)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of solvent

出典と根拠

ORDレコード
ord-96576979c9ae4945afe020f841ff44a7
出典データセット
uspto-grants-2003_04
特許番号
US06541467B1

反応ノート

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