Methyl iodide → HCID 86624979, compound

HRID 547260Notes

Reaction equation

HRID 547260 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N:23]4[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24]4)[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:36](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[CH3:36][N:16]1[C:17]2[C:22](=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:24]3)=[CH:19][CH:18]=2)[C:14]([S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:13])=[O:12])=[N:15]1.[CH3:36][N:15]1[C:14]([S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:13])=[O:12])=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([N:23]3[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:24]3)=[CH:21]2)=[N:16]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178454137HCID 178454137, compound

Product 2

HCID 86624979HCID 86624979, compoundYield 72%HCID 86624980HCID 86624980, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide solution of tert-butyl {(3R)-1-[3-(1-naphthylsulfonyl)-1H-indazol-5-yl]pyrrolidin-3-yl}carbamate (0.300 g, 0.609 mmol) was added cesium carbonate (0.198 g, 0.609 mmol). After 10 min, methyl iodide (0.046 mL, 0.104 mmol) was added and the reaction mixture was stirred for one hour. The reaction mixture was quenched with water, extracted with ethyl acetate (three times), dried over magnesium sulfate, concentrated and purified by column chromatography to afford tert-butyl {(3R)-1-[1-methyl-3-(naphthalen-1-ylsulfonyl)-1H-indazol-5-yl]pyrrolidin-3-yl}carbamate (223 mg, 72%) and tert-butyl {(3R)-1-[2-methyl-3-(naphthalen-1-ylsulfonyl)-2H-indazol-5-yl]pyrrolidin-3-yl}carbamate (53 mg, 17%)

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (three times)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-9c5539002c184009a20dce127273da76
Source dataset
uspto-grants-2011_05
Patent number
US07939520B2

Reaction notes

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