2-Bromopropionitrile → Rac-2-[2-(1,1-dioxo-1lambda6-thiomorpholine-4-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-indol-1-yl]-propionitrile

HRID 493997Notes

Reaction equation

HRID 493997 reaction equation
[O:1]=[S:2]1(=[O:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.Br[CH:31]([CH3:34])[C:32]#[N:33]>>[O:29]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:11]([CH:31]([CH3:34])[C:32]#[N:33])[C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:27])[CH3:28])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 1405382-BromopropionitrileHCID 16739577(1,1-Dioxo-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone

Product 1

HCID 16739644Rac-2-[2-(1,1-dioxo-1lambda6-thiomorpholine-4-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-indol-1-yl]-propionitrile

Procedure

In analogy to the procedure described for the synthesis of example 1, step 1, the title compound was synthesized from (1,1-dioxo-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone (Example 2) and 2-bromopropionitrile. The desired product was obtained in a yield of 20% as a light yellow foam. MS (m/e): 473.6 (MH+, 100%).

Workup

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

Sources & evidence

ORD record
ord-3ce1b06df2804f8e9b47d963b468bf69
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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