Sodium hydride → tert-Butyl{1-[2-(7,8-difluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255318Notes

Reaction equation

HRID 255318 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:13])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24]1)(=O)=O.COC1C=C2C(C=CC(=O)N2CCN2CCC(NC(=O)OC(C)(C)C)CC2)=CC=1>C(OCC)(=O)C>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:13])[N:9]2[CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25][CH2:24]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateHCID 667734367,8-Difluoroquinoxalin-2(1H)-one2×

Product 1

HCID 86642645tert-Butyl{1-[2-(7,8-difluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateYield 14.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7,8-Difluoroquinoxalin-2(1H)-one (Intermediate 155—a mixture of regioisomers containing 30% 5,6-difluoroquinoxalin-2(1H)-one, 1.0 g, 5.50 mmol) was deprotonated with sodium hydride (60% in oil, 0.26 g, 6.60 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (6.6 mmol) as described for Intermediate 2. Chromatography on silica gel with 70-100% ethyl acetate in hexanes gave 320 mg of the product as a colorless solid.

Sources & evidence

ORD record
ord-935a592c35b540e19637740941dfefb4
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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