Pyridine → ethyl 5-(2-methoxyethoxy)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

HRID 2238985Notes

Reaction equation

HRID 2238985 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.N1C=CC=CC=1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[S:32](Cl)(=[O:34])=[O:33]>CO>[CH3:20][O:19][CH2:18][CH2:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:32]([C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)(=[O:34])=[O:33])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 855182-Thiophenesulfonyl chlorideHCID 57476192ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylate

Product 1

HCID 57476193ethyl 5-(2-methoxyethoxy)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylate (2.00 g) and pyridine (30 mL) was added thiophene-2-sulfonyl chloride (1.57 g) at 0° C., and the mixture was stirred at room temperature for 15 hr. The reaction methanol (98:2-95:5, volume ratio) to give the title compound (250 mg, yield 27%) as orange crystals.

Sources & evidence

ORD record
ord-075427dc609a4437a008ea50ccd27fbd
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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