(S)-8-Fluoro-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline → (S)-(6-Bromo-8-fluoro-5-hydroxy-2-methyl-3,4-dihydroquinolin-1 (2H)-yl)(cyclopropyl)methanone

HRID 1051574Notes

Reaction equation

HRID 1051574 reaction equation
[F:1]C1C=CC(OC)=C2C=1N[C@@H](C)CC2.[Br:15][C:16]1[CH:25]=[CH:24][C:23]2[N:22]([C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[C@@H:21]([CH3:31])[CH2:20][CH2:19][C:18]=2[C:17]=1[OH:32]>>[Br:15][C:16]1[C:17]([OH:32])=[C:18]2[C:23](=[C:24]([F:1])[CH:25]=1)[N:22]([C:26]([CH:28]1[CH2:30][CH2:29]1)=[O:27])[C@@H:21]([CH3:31])[CH2:20][CH2:19]2

Participants

3

Reactant 2

HCID 118075452(S)-8-Fluoro-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinolineHCID 118075707(2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol2×

Product 1

HCID 118086471(S)-(6-Bromo-8-fluoro-5-hydroxy-2-methyl-3,4-dihydroquinolin-1 (2H)-yl)(cyclopropyl)methanone

Procedure

(S)-(6-Bromo-8-fluoro-5-hydroxy-2-methyl-3,4-dihydroquinolin-1 (2H)-yl)(cyclopropyl)methanone was synthesized from (S)-8-fluoro-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline according to the procedures described above for (2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol (Intermediate 2, Steps 1a, 2a, and 3). MS (ESI, pos. ion) m/z 328, 330 [M+H]+.

Sources & evidence

ORD record
ord-18a37901c48c483b8fb57f5a1dd7d23d
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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