1-Bromo-3-methoxypropane → [6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1-(3-methoxy-propyl)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

HRID 493999Notes

Reaction equation

HRID 493999 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15][CH2:14]3)=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:21][CH:22]1[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]1.Br[CH2:32][CH2:33][CH2:34][O:35][CH3:36]>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15][CH2:14]3)=[O:12])[N:8]2[CH2:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:4][C:3]=1[O:21][CH:22]1[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 5245511-Bromo-3-methoxypropaneHCID 16739609[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-methanone

Product 1

HCID 16739645[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1-(3-methoxy-propyl)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of example 1, step 1, the title compound was synthesized from [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-methanone (Example 6, step 4) and 1-bromo-3-methoxypropane. The desired product was obtained in a yield of 65% as light yellow foam. MS (m/e): 570.4 (M+H, 70%).

Workup

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

Sources & evidence

ORD record
ord-5b432fa072b34c848e6cc5f6fd3f4aea
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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