Sodium hydride → 6-{(SR)-1-[(3RS,4SR)-1-(1-Cyanomethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[CH:22]([O:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=2)[CH3:23])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].I[CH2:36][C:37]#[N:38]>C1COCC1>[C:37]([CH2:36][N:19]1[CH2:20][CH2:21][CH:16]([C:14]([N:12]2[CH2:13][CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH:10]([CH:22]([O:24][C:25]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=3)[CH3:23])[CH2:11]2)=[O:15])[CH2:17][CH2:18]1)#[N:38]