Sodium hydride → tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 1644302Notes

Reaction equation

HRID 1644302 reaction equation
FC1C=C2C(C=CC(=O)N2)=CC=1.[H-].[Na+].CS(OCCN1CCC(NC(OC(C)(C)C)=O)CC1)(=O)=O.[C:36]([O:40][C:41](=[O:64])[NH:42][CH:43]1[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][N:51]2[C:60]3[C:55](=[CH:56][CH:57]=[C:58]([F:62])[C:59]=3F)[CH:54]=[CH:53][C:52]2=[O:63])[CH2:45][CH2:44]1)([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:41](=[O:64])[NH:42][CH:43]1[CH2:44][CH2:45][N:46]([CH2:49][CH2:50][N:51]2[C:60]3[C:55](=[CH:56][CH:57]=[C:58]([F:62])[CH:59]=3)[CH:54]=[CH:53][C:52]2=[O:63])[CH2:47][CH2:48]1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 190675757-Fluoroquinolin-2(1H)-one2×HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 86642603tert-butyl{1-[2-(7,8-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 86635312tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Procedure

7-Fluoroquinolin-2(1H)-one (Intermediate 29) (500 mg, 3.06 mmol) was deprotonated with sodium hydride (135 mg, 60% in oil, 3.37 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (3.7 mmol) as described for Intermediate 20. Colorless solid, 570 mg (48%).

Sources & evidence

ORD record
ord-7bf3f3ecaee44b44bf3c95a5da864c90
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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