Triethylamine → Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester

HRID 1633636Notes

Reaction equation

HRID 1633636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][O:22][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 186795225-[1-(4-Fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol

Product 1

HCID 86585584Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl esterYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

440 mg (1.5 mmol) 5-[1-(4-Fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol in 15 ml CH2Cl2 were treated with 0.15 ml (1.8 mmol) methane sulfonyl chloride and 0.63 ml (4.5 mmol) triethyl amine at 0° C. for 10 min. The solution was stirred at RT for 2 h and was diluted with CH2Cl2. The organic phase was extracted with 1M HCl and water, and dried over Na2SO4. Evaporation yielded 400 mg (71%) Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester as light yellow viscous oil, MS: 372 (MH+).

Workup

  1. extractionThe organic phase was extracted with 1M HCl and water
  2. dry with materialdried over Na2SO4
  3. customEvaporation

Sources & evidence

ORD record
ord-4dfa045a5aef4fb689b5efa7ca2d9af2
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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