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N-[3-[2-(diisopropylamino)ethoxy]-4-methoxypheny]-4-iodobenzamide → N-[3-[2-[Bis(1-methylethyl)amino]ethoxy]-4-methoxyphenyl]-4-(2-thienyl)benzamide

HRID 2185021
Notes
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Reaction equation

HRID 2185021 reaction equation
[Br-].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[Zn+].[CH:8]([N:11]([CH:33]([CH3:35])[CH3:34])[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22])([CH3:10])[CH3:9]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][CH:33]([N:11]([CH:8]([CH3:10])[CH3:9])[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][C:24](=[O:32])[C:25]2[CH:26]=[CH:27][C:28]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)=[CH:29][CH:30]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 18672563N-[3-[2-(diisopropylamino)ethoxy]-4-methoxypheny]-4-iodobenzamideHCID 178419761HCID 178419761, compound

Product 1

HCID 22459309N-[3-[2-[Bis(1-methylethyl)amino]ethoxy]-4-methoxyphenyl]-4-(2-thienyl)benzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of 2-thienylzinc bromide in tetrahydrofuran (0.5M, 5 mL, 2.5 mmol) was added to a solution of N-[3-[2-(diisopropylamino)ethoxy]-4-methoxypheny]-4-iodobenzamide (WO 99/01127) (0.5 g, 1 mmol) in tetrahydrofuran (5 mL) containing tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.06 mmol), and the mixture was stirred at RT for 16 h. The reaction was quenched with saturated ammonium chloride and extracted with ether and dichloromethane. The organic phase was dried (MgSO4), concentrated in vacuo, and chromatographed (silica gel, 5% methanol/dichloromethane) to afford the title compound (0.1 g) MS(ES) m/e 452.8 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with ether and dichloromethane
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed (silica gel, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-29b6ff22035b4f50999b27152e1870bd
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06399656B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes