Triethylamine → 5-(2-Methanesulfonyloxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966481Notes

Reaction equation

HRID 966481 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH2:13]([O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][OH:34])[CH:30]=2)[NH:25][C:24]=1[C:35]([F:38])([F:37])[F:36])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][O:34][S:2]([CH3:1])(=[O:4])=[O:3])[CH:30]=2)[NH:25][C:24]=1[C:35]([F:37])([F:36])[F:38])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 233938735-(2-hydroxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 233938765-(2-Methanesulfonyloxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic Acid Benzyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.1 mL, 1.15 mmol, 1 eq) and triethylamine (0.32 mL, 2.30 mmol, 2 eq) were added to 5-(2-hydroxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic acid benzyl ester (420 mg, 1.15 mmol, 1 eq) obtained from previous step in THF (50 mL) solution in 100-mL round bottom flask at room temperature. The reaction mixture was stirred at room temperature for 3 hours (followed by TLC). After the solvent was removed, the residue was dissolved in ethyl acetate (100 mL), and then washed with sat NaHCO4 and brine respectively. The organic layer was dried over MgSO4, and concentrated to give a pale brown solid. The crude was carried over to the next step.

Workup

  1. customAfter the solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto give a pale brown solid

Sources & evidence

ORD record
ord-f91f2dbc5b594603917b2246cff16c3a
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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