Sodium Hydroxide → n-[3-(4-Cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide

HRID 48369Notes

Reaction equation

HRID 48369 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[C:11]1([CH2:17][O:18][C:19]([NH:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[OH-].[Na+]>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].OO>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH2:24][CH2:23][CH2:22][NH:21][C:19]([O:18][CH2:17][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:20])=[CH:3][C:4]=1[F:10])#[N:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 562279Benzyl allylcarbamateHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 22743232n-[3-(4-Cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 784Hydrogen PeroxideSolvent

Procedure

Scheme IIIb, step A: 4-Bromo-2-fluorobenzonitrile (3 g, 15 mmol), (phenylmethoxy)-N-prop-2-enylcarboxamide (3.44 g, 18 mmol), 9-BBN dimer (2.93 g, 12 mmol), [1,1′bis(diphenylphosphino)ferrocene] dichloropalladium (II), PdCl2(dppf) (0.61 g, 0.75 mmol), 3N sodium hydroxide (10 mL), and pH=7 buffer: hydrogen peroxide (2:1, 20 mL) are combined in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, N-[3-(4-cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide, (4.18, 89%). Electron spray M.S. 313 (M*+H).

Sources & evidence

ORD record
ord-85b4343d051f4722b9e36dfdc0357a60
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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