Water → 4-[1-(2-chlorophenyl)-2-(4-methoxyphenyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridin-5-yl]benzonitrile

HRID 1790034Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].F[C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:32]3[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=3)[CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 80.0 mg, 0.236 mmol) and K2CO3 (97.9 mg, 0.708 mmol) in 2 mL DMF was added 4-fluorobenzonitrile (86.0 mg, 0.472 mmol) under argon. The mixture was heated at 130° C. with stirring for 48 h. The mixture was cooled to rt, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified on silica gel eluting with 1:3 EtOAc/hexanes to give a solid (44.7 mg, 43%): Rf=0.32 (1:2 EtOAc/hexanes).

Workup

temperatureThe mixture was cooled to rt
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
customevaporated under reduced pressure
customThe crude product was purified on silica gel eluting with 1:3 EtOAc/hexanes

Sources & evidence

ORD record: ord-6157255225ff4b5cbcd857cbe125149b
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071207B2

Reaction notes

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