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

HRID 855635노트

반응식

HRID 855635 반응식
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]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178434347HCID 178434347, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b297e9401ab4c09a2cfbaea5bfcf9bb
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262203B2

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