Boron tribromide → HCID 68678757, compound

HRID 1443213Notes

Reaction equation

HRID 1443213 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][NH:26][C:27]2=[O:32].B(Br)(Br)Br>>[OH:18][C:11]1([C:14]([F:17])([F:15])[F:16])[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][NH:26][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][NH:26][C:27]2=[O:32]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 123410025-amino-1(2H)-phthalazinoneHCID 179890984-(2-Methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 2

HCID 68678757HCID 68678757, compoundHCID 86599922HCID 86599922, 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 277 mg of 5-amino-phthalazin-1-one. As in Example 2, 32 mg of 5-{[2-hydroxy-4,4-dimethyl-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalazin-1(2H)-one as fraction 1 and 35 mg of 5-{[2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalazin-1(2H)-one as fraction 3 are obtained by reaction of 470 mg of imine with 5.4 ml of BBr3 (1 M in dichloromethane).

Sources & evidence

ORD record
ord-b8bfe344ffb94da7b5a794f7c6e6855e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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