Diisopropylethylamine → Methyl 2-(3-(bis(4-methoxyphenyl)methylamino)-2-nitrophenoxy)-4-fluorobenzoate

HRID 573159Notes

Reaction equation

HRID 573159 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](F)[C:14]=2[N+:20]([O-:22])=[O:21])[CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[NH2:32])=[CH:27][CH:26]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([CH:31]([NH:32][C:15]2[C:14]([N+:20]([O-:22])=[O:21])=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3500424,4'-DimethoxybenzhydrylamineHCID 67227494Methyl 4-fluoro-2-(3-fluoro-2-nitrophenoxy)benzoate

Product 1

HCID 67146178Methyl 2-(3-(bis(4-methoxyphenyl)methylamino)-2-nitrophenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of EXAMPLE 368A (1.33 g), bis(4-methoxyphenyl)methanamine (1.046 g) and N-ethyl-N-isopropylpropan-2-amine (1.127 ml) in anhydrous 1-methyl-2-pyrrolidinone (20 mL) was stirred at 120° C. overnight. The mixture was concentrated and the residue was taken up in water (100 mL) and extracted with dichloromethane. The residue was absorbed on silica and purified by chromatography on a silica gel column, eluting with 25% ethyl acetate in hexane to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with dichloromethane
  3. customThe residue was absorbed on silica
  4. custompurified by chromatography on a silica gel column
  5. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ab76e48681a2416f9952622c53898e37
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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