Diisopropylethylamine → 6-Bromo-7-fluoro-N-(4-methyloxan-4-yl)-3-nitroquinolin-4 amine

HRID 1486939Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([N+:13]([O-:15])=[O:14])=[C:5]2Cl.Cl.[CH3:18][C:19]1([NH2:25])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([N+:13]([O-:15])=[O:14])=[C:5]2[NH:25][C:19]1([CH3:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Bromo-4-chloro-7-fluoro-3-nitroquinoline (1 g, 3.27 mmol) was added to a solution of 4-methyltetrahydro-2H-pyran-4-amine hydrochloride (0.596 g, 3.93 mmol) and DIPEA (1.715 mL, 9.82 mmol) in DMA (10 mL) and the resulting mixture stirred at 100° C. for 4 h. The reaction mixture was diluted with water and the solid collected by filtration and dried to afford the desired material (1.215 g, 97%) as a brown solid which was used without further purification.

Workup

filtrationthe solid collected by filtration
customdried

Sources & evidence

ORD record: ord-8777e43e04984b54bcc7a5046ee45fb2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428503B2

Reaction notes

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