Boron tribromide → HCID 68679535, compound

HRID 1443214Notes

Reaction equation

HRID 1443214 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH3:20])([CH3:19])[CH2:10][C:11]([OH:18])([C:14]([F:17])([F:16])[F:15])[CH:12]=O.[NH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[N:25][N:26]([CH3:33])[C:27]2=[O:32].B(Br)(Br)Br>>[OH:18][C:11]1([C:14]([F:16])([F:15])[F:17])[CH2:10][C:9]([CH3:19])([CH3:20])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:12]1[NH:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[N:25][N:26]([CH3:33])[C:27]2=[O:32].[OH:18][C:11]1([C:14]([F:15])([F:16])[F:17])[CH2:10][C:9]([CH3:19])([CH3:20])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[CH:12]1[NH:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[N:25][N:26]([CH3:33])[C:27]2=[O:32]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 179850455-Amino-2-methylphthalazin-1-oneHCID 17989098HCID 17989098, compound

Product 2

HCID 68679535HCID 68679535, compoundHCID 86599923HCID 86599923, compound

Procedure

Analogously to Example 10, the corresponding imine is produced starting from 500 mg of 4-(2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 302 mg of 5-amino-2-methylphthalazin-1-one. As in Example 2, 158 mg of 5-{[2-hydroxy-4,4-dimethyl-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-2-methylphthalazin-1-one as fraction 1, 66 mg of 5-{[2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-2-methylphthalazin-1-one, diastereomer A as fraction 4, and 77 mg of 5-{[2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-2-methylphthalazin-1-one, diastereomer A as fraction 5 are obtained by reaction of 570 mg of imine with 6.4 ml of BBr3 (1 M in dichloromethane).

Sources & evidence

ORD record
ord-6fe6e62d9523495cb8dd104b8c9b93ca
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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