N-methyl-2-pyrrolidone → 3-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

HRID 1387088Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:25]=1.[Cu][C:27]#[N:28].[CH3:29][N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=O>[Cl-].[Na+].O>[C:27]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:25][C:3]=1[CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:10][C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][C:7]=2[S:8][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:16]=1)#[N:28]

Participants

Conditions

Temperature: 200 °C

Procedure

A suspension of 3-[3-bromo-4-[(1-pyrrolidinyl)]methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (158 mg, 0.26 mmol) and copper(I) cyanide (40 mg) in 1-methyl-2-pyrrolidinone (3 mL) was allowed to stir at 200° C. under nitrogen for 5 h. The cooled reaction mixture was diluted with brine (50 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography of the residue with Et3N:MeOH:EtOAc (5:5:90) afforded the product (64 mg, 44%).

Workup

customThe cooled reaction mixture
extractionextracted with EtOAc (50 mL×3)
dry with materialThe combined organic layers were dried with sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-38826372dd8f4f229215da212374395e
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Reaction notes

Loading…