Methyl iodide → HCID 58812060, compound

HRID 2240022Notes

Reaction equation

HRID 2240022 reaction equation
CI.[C:3]1([S:13]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH2:26][CH2:27][O:28][S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[CH:23]=3)[NH:18][N:17]=2)(=[O:15])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:39](=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:39][N:18]1[C:19]2[C:24](=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][S:29]([C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=3)(=[O:30])=[O:31])=[CH:21][CH:20]=2)[C:16]([S:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)(=[O:14])=[O:15])=[N:17]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178427773HCID 178427773, compound

Product 1

HCID 58812060HCID 58812060, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyliodide (0.06 mL, 0.96 mmol) was added to a chilled mixture of toluene -4-sulfonic acid 2-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.401 g, 0.767 mmol) and cesium carbonate (0.29 g, 0.89 mmol) in acetone (10 mL). The reaction mixture was stirred at ambient temperature under nitrogen for 3 hours. It was then partitioned in ethyl acetate and water. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography with 25-40% ethyl acetate in hexane, 100% chloroform and 1% methanol in chloroform. Drying at 65° C. in vacuo for yielded toluene-4-sulfonic acid 2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester as a buff foam (0.224 g, 54.4%). 1HNMR (400 MHz, DMSO-d6): δ8.27 (d, 1H, J=8.54 Hz), 8.55 (dd, 1H, J=7.42 Hz and 1.16 Hz), 8.30 (d, 1H, J=8.35 Hz), 8.05-8.07 (m, 1H), 7.72-7.76 (m, 3H), 7.60-7.70 (m, 3H), 7.31 (d, 2H, J=8.01 Hz), 7.18 (d, 1H, J=2.20 Hz), 7.00-7.03 (m, 1H), 4.35-4.37 (m, 2H), 4.22-4.24 (m, 2H), 4.07 (s, 3H), 2.28 ppm (s, 3H).

Workup

  1. customIt was then partitioned in ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography with 25-40% ethyl acetate in hexane, 100% chloroform and 1% methanol in chloroform
  7. customDrying at 65° C. in vacuo

Sources & evidence

ORD record
ord-164f50d9522347329ef0fbbba26d9654
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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