Sodium Dithionite → (R)-N2-(1-Cyclopropyl-propyl)-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-pyridine-2,3-diamine

HRID 1831543Notes

Reaction equation

[CH:1]1([C@H:4]([NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[C:12]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([O:24][CH3:25])=[CH:19][C:18]=3[CH3:26])[CH:11]=[CH:10][N:9]=2)[CH2:5][CH3:6])[CH2:3][CH2:2]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[CH:1]1([C@H:4]([NH:7][C:8]2[C:13]([NH2:14])=[C:12]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([O:24][CH3:25])=[CH:19][C:18]=3[CH3:26])[CH:11]=[CH:10][N:9]=2)[CH2:5][CH3:6])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 69658188(R)-(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine

Product 1

HCID 69658258(R)-N2-(1-Cyclopropyl-propyl)-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-pyridine-2,3-diamineYield 98%

Procedure

(R)-(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine (0.17 g, 0.47 mmol) and Na2S2O4 (1.24 g, 7.10 mmol) were treated as in Part E of Example 9 to give 0.15 g (98%) crude (R)-N2-(1-Cyclopropyl-propyl)-4-(5-fluoro-4-methoxy-2-methyl-phenyl)-pyridine-2,3-diamine.

Sources & evidence

ORD record: ord-dffd7005cfab4a9589ac9679359b37de
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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