Triethylamine → Methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate

HRID 852614Notes

Reaction equation

HRID 852614 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:16][CH3:17].CCN([CH2:23][CH3:24])CC.[Cl:25][CH2:26][CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Cl:25][CH2:26][CH2:27][CH2:28][S:29]([N:2]([S:29]([CH2:28][CH2:23][CH2:24][Cl:1])(=[O:31])=[O:30])[C:3]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:16][CH3:17])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 69359674methyl 4-amino-1-ethyl-1H-indole-6-carboxylate hydrochloride

Product 1

HCID 69357512Methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylateYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-amino-1-ethyl-1H-indole-6-carboxylate hydrochloride salt (D202) (1.7 g, 6.68 mmol, 1 equiv) in CH2Cl2 (50 ml) was added NEt3 (4.2 ml, 30 mmol, 4.5 equiv) then 3-chloro-1-propanesulfonyl chloride (1.8 ml, 15.0 mmol, 2.2 equiv) and the resulting mixture was stirred for 2 h. The organic phase was washed with a 2N aqueous HCl solution and a saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/1) gave methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate (D236) (1.85 g, 55%) as a light tan solid. [M−H]−=498.1, RT=3.51 min.

Workup

  1. washThe organic phase was washed with a 2N aqueous HCl solution
  2. dry with materiala saturated aqueous NaHCO3 solution, dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/1)

Sources & evidence

ORD record
ord-3c71fab72f7e443fac5e8a6d86c64345
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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