N-bromobutanimide → HCID 86589691, compound

HRID 1828373Notes

Reaction equation

[CH3:1][C:2]([NH:8][C:9]([C:11]1[CH:36]=[CH:35][CH:34]=[CH:33][C:12]=1[C:13]([NH:15][C:16]1[C:17]([CH3:32])=[N:18][C:19]([O:22][CH:23]([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=1)=[O:14])=[O:10])([CH3:7])[CH:3]=[N:4][O:5][CH3:6].BrN1C(=O)CCC1=O.[I:45]N1C(=O)CCC1=O>>[CH3:7][C:2]([NH:8][C:9]([C:11]1[C:36]([I:45])=[CH:35][CH:34]=[CH:33][C:12]=1[C:13]([NH:15][C:16]1[C:17]([CH3:32])=[N:18][C:19]([O:22][CH:23]([C:28]([F:31])([F:29])[F:30])[C:24]([F:26])([F:27])[F:25])=[CH:20][CH:21]=1)=[O:14])=[O:10])([CH3:1])[CH:3]=[N:4][O:5][CH3:6]

Participants

Reactant 3

HCID 67184N-bromobutanimide

HCID 120273N-Iodosuccinimide

HCID 86589692HCID 86589692, compound

Product 1

HCID 86589691HCID 86589691, compoundYield 83%

Procedure

2-(1,1-Dimethyl-2-(N-methoxyimino)ethylaminocarbonyl)-N-(6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-2-methylpyridin-3-yl)benzamide was treated in the same manner as in Example 36, except that the N-bromosuccinimide was replaced with N-iodosuccinimide, to obtain 2-(1,1-dimethyl-2-(N-methoxyimino)ethylaminocarbonyl)-N-(6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-2-methylpyridin-3-yl)-3-iodobenzamide (yield 83%, melting point 220° C.). Regioselectivity of iodination into the 3-position was 100%.

Sources & evidence

ORD record: ord-c23e6fac663b41a297df327f2d2ec452
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07057067B2

Reaction notes

Loading…