4-Iodopyridine → 1-(3-Bromo-4-fluorophenyl)-4-fluoro-1-(pyridin-4-yl)-1H-isoindol-3-amine

HRID 1662184Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2[C:31]#[N:32])=[N:17]S(C(C)(C)C)=O)[CH:12]=[CH:13][C:14]=1[F:15]>>[Br:8][C:9]1[CH:10]=[C:11]([C:16]2([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[C:24]3[C:25](=[C:26]([F:30])[CH:27]=[CH:28][CH:29]=3)[C:31]([NH2:32])=[N:17]2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

Reactant 2

HCID 6094924-Iodopyridine

HCID 76821603N-((3-Bromo-4-fluorophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide

Product 1

HCID 585794771-(3-Bromo-4-fluorophenyl)-4-fluoro-1-(pyridin-4-yl)-1H-isoindol-3-amineYield 37%

Procedure

The title compound was synthesized as described for example 11i in 37% yield, starting from 4-iodopyridine (0.530 g, 2.59 mmol) and N-((3-bromo-4-fluorophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (1.00 g, 2.35 mmol).

Sources & evidence

ORD record: ord-eeb937762e0f40aabd10b52a24480f67
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030500B2

Reaction notes

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