Methyl iodide → HCID 66899438, compound

HRID 2369892Notes

Reaction equation

HRID 2369892 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:18])=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[N:6]1.[C:21](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:20][O:19][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:18][CH3:21])=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[N:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66899434HCID 66899434, compound

Product 1

HCID 66899438HCID 66899438, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1-(2,2-dimethoxyethyl)-5-hydroxy-1H-indazole-7-carboxylate (180 mg, 0.6 mmol) from Step F above in DMF (10 ml) was added cesium carbonate (313 mg, 1.0 mmol) followed by iodomethane (40 μL, 0.64 mmol) and the reaction was stirred overnight. The reaction mixture was extracted with ethyl acetate, washed with water, dried (Na2SO4), and concentrated in vacuo to afford methyl 1-(2,2-dimethoxyethyl)-5-methoxy-1H-indazole-7-carboxylate (180 mg, 96%): 1H NMR (500 MHz, CDCl3) δ 7.98 (s, 1H), 7.56 (d, J=2.5 Hz, 1H), 7.25 (d, J=2.5 Hz, 1H), 4.90 (d, J=5.0 Hz, 2H), 4.51 (d, J=5.0 Hz, 1H), 3.97 (s, 3H), 3.87 (s, 3H), 3.27 (s, 6H); MS (ESI+) m/z 295 (M+H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-535292baa61449ebb3e18357b27f4331
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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