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

HRID 493993Notes

Reaction equation

HRID 493993 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.[CH:31](CS([O-])(=O)=O)([CH3:33])[CH3:32]>>[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[CH:31]([CH3:33])[CH3:32])=[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 16739609[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-methanoneHCID 22141912Isopropyl-methanesulfonate

Product 1

HCID 16739675[6-Bromo-1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of example 3, 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 isopropylmethanesulfonate. The desired product was obtained in a yield of 69% as light yellow solid. MS (m/e): 540.3 (M+H, 100%).

Workup

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

Sources & evidence

ORD record
ord-6bf0ea85da1c4483a0f57755b6be77fd
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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