4-Bromo-2-(trifluoromethyl)pyridine → 1-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine

HRID 1662181Notes

Reaction equation

HRID 1662181 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[C:22]#[N:23])=[N:9]S(C(C)C)=O)[CH:7]=1.Br[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C:8]2([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:15]3[C:16](=[C:17]([F:21])[CH:18]=[CH:19][CH:20]=3)[C:22]([NH2:23])=[N:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 86641816HCID 86641816, compound

Product 1

HCID 585795381-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amineYield 90%

Procedure

The title compound was synthesized as described for example 11i in 90% yield starting from N-((5-bromo-2-fluorophenyl)(2-cyano-3-fluorophenyl)methylene)propane-2-sulfinamide (0.980 g, 2.38 mmol) and 4-bromo-2-(trifluoromethyl)pyridine (0.646 g, 2.86 mmol). Purification was achieved by flash chromatography using a gradient of 100% CH2Cl2 to 30% 0.1M NH3 in MeOH in CH2Cl2.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-f858d39b5c884b4e81518b1d6bac0ef5
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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