Indomethacin → Indole-3-acetamide, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-

HRID 2394239Notes

Reaction equation

[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23](O)=[O:24].C([N:28](CC)CC)C.C(OC(Cl)=O)C(C)C>C1COCC1>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([N:10]2[C:9]3[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=3)[C:3]([CH2:22][C:23]([NH2:28])=[O:24])=[C:2]2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Indomethacin (10 g; 0.028 mol) in 150 mL THF was treated with triethylamine (4.8 mL; 0.035 mol) and cooled to -10° C. Isobutylchloroformate (4.4 mL; 0.033 mol) was added and the reaction was stirred at -10° C. for 10 min. The ice bath was removed and NH3 was bubbled through the solution for 15 min. The resulting pale yellow solid was collected, slurried in CH2Cl2 and filtered again. The product was used with no further purification.

Workup

customThe ice bath was removed
customNH3 was bubbled through the solution for 15 min
customThe resulting pale yellow solid was collected
filtrationfiltered again
customThe product was used with no further purification

Sources & evidence

ORD record: ord-b859e7b303ba46f2b03b17062cd1a83c
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811425

Reaction notes

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