Thiomorpholine 1,1-dioxide → (1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-(5-hydroxy-1-isopropyl-1H-indol-2-yl)-methanone

HRID 494006Notes

Reaction equation

HRID 494006 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]([C:14]([OH:16])=O)=[CH:5]2.[NH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[CH2:19][CH2:18]1>>[O:23]=[S:20]1(=[O:24])[CH2:21][CH2:22][N:17]([C:14]([C:6]2[N:7]([CH:11]([CH3:12])[CH3:13])[C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=3)=[O:16])[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 670735755-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid

Product 1

HCID 67073360(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-(5-hydroxy-1-isopropyl-1H-indol-2-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of example 1, step 3, the title compound was synthesized from 5-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid (Example 20, step 3) and thiomorpholine-1,1-dioxide (purchased at Syntec, ref. M1201). The desired product was obtained in a yield of 75% as white solid. MS (m/e): 335.5 (M−H, 100%).

Workup

  1. customIn analogy to the procedure described for the synthesis of example 1, step 3

Sources & evidence

ORD record
ord-187a159902a3411db44302f561b59e80
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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