Bromoacetonitrile → [2-(4,4-Difluoro-piperidine-1-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridin-1-yl]-acetonitrile

HRID 1437719Notes

Reaction equation

HRID 1437719 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:28][C:13]3=[N:14][CH:15]=[C:16]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]4)[CH:17]=[C:12]3[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:33][C:34]#[N:35]>>[F:29][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:28]([CH2:33][C:34]#[N:35])[C:13]3=[N:14][CH:15]=[C:16]([O:18][CH:19]4[CH2:20][CH2:21][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:23][CH2:24]4)[CH:17]=[C:12]3[CH:11]=2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 16727356(4,4-Difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-methanone

Product 1

HCID 16727137[2-(4,4-Difluoro-piperidine-1-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridin-1-yl]-acetonitrileYield 61%

Procedure

The title compound was synthesized in analogy to example 18 from (4,4-difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]methanone (example 13), sodium hydride and bromoacetonitrile, to give the desired product as a light yellow oil (61%).

Sources & evidence

ORD record
ord-545bec8f62464dc585b5fc22127395d8
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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