Sodium borohydride → 5-{[1-(3,4-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-2-fluorophenylamine

HRID 2269462Notes

Reaction equation

HRID 2269462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([N+:28]([O-])=O)[CH:22]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([NH2:28])[CH:22]=2)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18347053N-[1-(3,4-Difluorophenyl)ethyl]-N-[(4-fluoro-3-nitrophenyl)-(4-methoxyphenyl)methyl}amine

Product 1

HCID 183342665-{[1-(3,4-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-2-fluorophenylamineYield 78.4%

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a similar procedure to that described in Example (1b), 2.5 g of N-[1-(3,4-difluorophenyl)ethyl]-N-[(4-fluoro-3-nitrophenyl)-(4-methoxyphenyl)methyl]amine [prepared as described in step (a) above], 3.29 g of nickel chloride hexahydrate and 957 mg of sodium borohydride were reacted, to obtain 1.82 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-efae7676064a4463b814951adfd33435
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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