4-Toluenesulfonyl chloride → HCID 58763427, compound

HRID 858289Notes

Reaction equation

HRID 858289 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH3:26])=[O:24])[CH:18]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH3:26])=[O:24])[CH:18]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][O:16][S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58763430HCID 58763430, compound

Product 1

HCID 58763427HCID 58763427, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-Hydroxy-ethyl)-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid methyl ester (0.41 g, 1.16 mmol), TsCl (0.23 g, 1.22 mmol), triethylamine (0.2 mL, 1.4 mmol) in dichloromethane (10 mL) was stirred at room temperature for 48 h. The solvent was removed under reduced pressure and the residue dissolved in EtOAc. The organic solution was washed with 10% KHSO4, dried over Na2SO4, and purified by silica gel chromatography (hexanes/EtOAc, 1/2) to give 0.37 g of 1-(3-methoxycarbonyl-phenyl)-3-[2-(toluene-4-sulfonyloxy)-ethyl]-1H-indole-2-carboxylic acid methyl ester as a yellow oil (63% yield): 1H NMR (CDCl3, 300 MHz) δ 2.37 (s, 3H), 3.52 (t, J=7.24 Hz, 2H), 3.67 (s, 3H), 3.92 (s, 3H), 4.34 (t, J=7.06, 2H), 7.00 (d, J=8.24 Hz, 1H), 7.17–7.31(m, 4H), 7.44 (d, J=8.02 Hz, 1H), 7.56–7.67(m, 4H), 7.93 (t, J=1.72 Hz, 1H); 8.13 (dt, J=7.82, 1.34 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic solution was washed with 10% KHSO4
  4. dry with materialdried over Na2SO4
  5. custompurified by silica gel chromatography (hexanes/EtOAc, 1/2)

Sources & evidence

ORD record
ord-899bd4ae9668419496bd99ea4da55604
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

Loading…