Water → 6-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole

HRID 1634073ノート

反応式

HRID 1634073 の反応式
Br[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1)=[N+:19]=[N-:20]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 186161856-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazole

生成物 1

HCID 186161896-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole収率 83%

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 6-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (4.0 g, 14 mmol) (6) in DMF (30 mL) was added sodium azide (6 g, 92 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution was 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 an yellow oil which was purified by column chromatography to yield title compound (2.91 g, 83%). TLC Rf 0.31 (70:30 of hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ1.75 (m, 3H), 2.10 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.01 (m, 1H), 4.48 (s, 2H), 5.73 (dd, 1H, J=8.2, 2.8 Hz), 7.12 (dd, 1H, J=8.2, 0.8 Hz), 7.55 (s, 1H), 7.71 (d, 1H, J=8.2 Hz), 8.02 (s, 1H).

後処理

  1. customa yellow solution was 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 materialthen dried (MgSO4)
  6. customEvaporation of solvent
  7. customgave an yellow oil which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-3dbd32136c134501a5aa1f4041b088e8
出典データセット
uspto-grants-2003_01
特許番号
US06506754B1

反応ノート

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