3-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine → 3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

HRID 912013Notes

Reaction equation

HRID 912013 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([N+:23]([O-])=O)=[C:10]([O:11][CH:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1>[Fe].Cl>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1

Participants

3

Reactant 1

HCID 578123503-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine2×

Product 1

HCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Reagents, catalysts & solvents 1

HCID 86633186Hydrochloric acid-ironCatalyst

Procedure

3-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine (Intermediate 9a) was reacted with iron/HCl as described in Example 2 to give 3-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (=racemic Example 2).

Sources & evidence

ORD record
ord-d2089770822b4bf9bd2dd1a710d054bd
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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