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

HRID 855635Notes

Reaction equation

HRID 855635 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8b297e9401ab4c09a2cfbaea5bfcf9bb
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

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