Bromoacetonitrile → {2-(4,4-Difluoro-piperidine-1-carbonyl)-5-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-pyrrolo[2,3-b]pyridin-1-yl}-acetonitrile

HRID 1437725Notes

Reaction equation

HRID 1437725 reaction equation
[F:1][C:2]1([F:33])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:28](S(C)(=O)=O)[C:13]3=[N:14][CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:27])[CH:17]=[C:12]3[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:37][C:38]#[N:39]>>[F:1][C:2]1([F:33])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:28]([CH2:37][C:38]#[N:39])[C:13]3=[N:14][CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:27])[CH:17]=[C:12]3[CH:11]=2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 16727134(4,4-Difluoro-piperidin-1-yl)-{1-methanesulfonyl-5-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-1H-pyrrolo[2,3-b]pyridin-2-yl}-methanone

Product 1

HCID 68422349{2-(4,4-Difluoro-piperidine-1-carbonyl)-5-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-pyrrolo[2,3-b]pyridin-1-yl}-acetonitrileYield 3%

Procedure

The title compound was synthesized in analogy to example 18 from (4,4-difluoro-piperidin-1-yl)-{1-methanesulfonyl-5-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-1H-pyrrolo[2,3-b]pyridin-2-yl}-methanone (example 20), sodium hydride and bromoacetonitrile, to give the desired product as a light yellow oil (3%).

Sources & evidence

ORD record
ord-2655e61b3162497f898851b25fef5a82
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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