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

HRID 1831546Notes

Reaction equation

[F:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([CH3:24])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C@@H:15]([CH2:18][O:19][CH3:20])[CH2:16][CH3:17])[C:9]=2[N+:21]([O-])=O)[CH:7]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[F:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([CH3:24])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C@@H:15]([CH2:18][O:19][CH3:20])[CH2:16][CH3:17])[C:9]=2[NH2:21])[CH:7]=1

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 69658289(R)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

Product 1

HCID 69658079(R)-4-(5-Fluoro-4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamineYield 102.3%

Procedure

(R)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine (0.16 g, 0.44 mmol) and Na2S2O4 (1.15 g, 6.6 mmol) were treated as in Part E of Example 9 to give 0.15 g (98%) crude (R)-4-(5-Fluoro-4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine. MS (AP) m/z 334.3 [(M+H)+, 100].

Sources & evidence

ORD record: ord-01a7afc6bec74733be00a6ca3555e99b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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