Boron tribromide → 5-{[2,5-Dihydroxy-4,4-dimethyl-6-fluoro-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-one

HRID 1443192Notes

Reaction equation

HRID 1443192 reaction equation
[F:1][C:2]1[C:3]([O:20]C)=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:33])[NH:28]2.B(Br)(Br)Br>>[OH:17][C:10]1([C:13]([F:15])([F:16])[F:14])[CH2:9][C:8]([CH3:18])([CH3:19])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[OH:20])[CH:11]1[NH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:33])[NH:28]2

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 157190785-Amino-1,2-dihydroquinolin-2-oneHCID 179890864-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 1

HCID 247811635-{[2,5-Dihydroxy-4,4-dimethyl-6-fluoro-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-oneYield 18%

Procedure

Analogously to Example 2, the corresponding imine is produced starting from 1.0 g of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal (Example 3) and 520 mg of 5-aminoquinolin-2(1H)-one. 255 mg of the title compound is obtained by reaction of 300 mg of imine with 3.3 ml of BBr3 (1N in dichloromethane).

Sources & evidence

ORD record
ord-b1d05c269fa6429ea3c4db6ba5ddac2e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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