Cesium carbonate → N,3-dimethyl-1H-indazol-6-amine

HRID 855635ノート

反応式

HRID 855635 の反応式
ClC1N=[C:6]([N:8](C)[C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH3:18])=[N:14][NH:15]3)=[CH:11][CH:10]=2)C=CN=1.C([O-])([O-])=O.[Cs+].[Cs+].ClC1C=C(C=CC=1)CBr>CN(C=O)C.C(OCC)(=O)C>[CH3:6][NH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH:17]=1)=[N:15][NH:14][C:13]=2[CH3:18]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178434347HCID 178434347、化合物

生成物 1

HCID 21956372N,3-dimethyl-1H-indazol-6-amine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-(2-chloropyrimidin-4-yl)-N,3-dimethyl-1H-indazol-6-amine (2 g, 7.31 mmol) was dissolved in DMF (15 ml), and Cs2CO3 (2 g, 14.6 mmol) and 3-chlorobenzyl bromide (1.25 ml, 9.5 mmol) were added at room temperature. Mixture was stirred at rt for overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was separated. The aqueous layer was thoroughly extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated to give 2-(3-chlorobenzyl)-N-2-chloropyrimidin-4-yl)-N,3-dimethyl-2H-indazol-6-amine as an off-white solid. 1H NMR (300 MHz, d6DMSO) δ 7.94 (d, J=6.0 Hz, 1H), 7.83 (d, J=8.8 Hz, 1H), 7.56 (d, J=1.3 Hz, 1H), 7.36-7.38 (m, 2H), 7.32 (br s, 1H), 7.16 (m, 1H), 6.91 (m, 1H), 6.28 (d, J=6.1 Hz, 1H), 5.65 (s, 2H), 3.42 (s, 3H), 2.63(s, 3H). MS (ES+, m/z) 398 (M+H).

後処理

  1. washwashed with water
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was thoroughly extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-8b297e9401ab4c09a2cfbaea5bfcf9bb
出典データセット
uspto-grants-2007_08
特許番号
US07262203B2

反応ノート

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