Cesium carbonate → HCID 21956335, compound

HRID 2265874Notes

Reaction equation

HRID 2265874 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:19])[C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH3:18])=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br>CN(C=O)C.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][N:14]1[C:13]([CH3:18])=[C:12]2[C:16]([CH:17]=[C:9]([N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH3:19])[CH:10]=[CH:11]2)=[N:15]1

Participants

6

Reactant 3

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

Product 1

HCID 21956335HCID 21956335, compound

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-80e3f328187b41bbbaffb41373b1748c
Source dataset
uspto-grants-2010_12
Patent number
US07858626B2

Reaction notes

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