Potassium Fluoride → tert-Butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate

HRID 452316Notes

Reaction equation

[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:25]=[C:24]([N+]([O-])=O)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:12][CH:11]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[F-:29].[K+]>>[F:29][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[CH:11][CH:12]=2)[CH:25]=1

Participants

Reactant 2

HCID 522689Potassium Fluoride

HCID 58362579Tert-butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate

Product 1

HCID 58362549tert-Butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate

Procedure

tert-Butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate was prepared using general procedure M from tert-butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate (10 mg, 0.026 mmol) and KF (60 mg, 1 mmol). tert-butyl (4-(4-fluoroquinolin-2-yl)phenyl)(methyl)carbamate was isolated as a clear oil (4.5 mg, 49%). 1H NMR (400 MHz, CDCl3): δ 8.16 (m, 1H), 8.12-8.07 (m, 3H), 7.78 (m, 1H), 7.59-7.54 (m, 2H), 7.41 (m, 1H), 3.32 (s, 3H), 1.48 (s, 9H); MS (ESI): 353 (M+H+).

Workup

customtert-Butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate was prepared

Sources & evidence

ORD record: ord-e50fdc080e1d4897a351a1f930d83d1a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08491869B2

Reaction notes

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