(5-Bromo-3-fluoro-2-methyl-phenyl)-acetic acid → 3-(5-Bromo-3-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

HRID 1962382Notes

Reaction equation

HRID 1962382 reaction equation
[Br:1][C:2]1[C:3](F)=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[NH:10][C:11]3([CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]3)[C:12]=2[OH:13])[CH:7]=1.BrC1C=C([F:36])C(C)=C(CC(O)=O)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([F:36])[C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[NH:10][C:11]3([CH2:14][CH2:15][N:16]([O:19][CH3:20])[CH2:17][CH2:18]3)[C:12]=2[OH:13])[CH:7]=1

Participants

3

Reactant 2

HCID 58083211(5-Bromo-3-fluoro-2-methyl-phenyl)-acetic acidHCID 596145973-(5-Bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

Product 1

HCID 580832043-(5-Bromo-3-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

Procedure

3-(5-Bromo-3-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound F3) was prepared analogously to the synthesis of 3-(5-bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (preparation example P5, step P5.5) starting from (5-bromo-3-fluoro-2-methyl-phenyl)-acetic acid (preparation example P7, step P7.2) by making use of the procedures described under step P5.4 and step P5.5. The title compound F3 was obtained as a solid.

Sources & evidence

ORD record
ord-459e023d2f104d8e8d286358b78db2eb
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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