3,4-Dimethoxyaniline → HCID 69507377, compound

HRID 1350190Notes

Reaction equation

HRID 1350190 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[NH2:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13]([NH:27][C:26]1[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:24]([O:23][CH3:22])[CH:25]=1)=[O:15]

Participants

6

Reactant 3

HCID 227703,4-DimethoxyanilineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69507184HCID 69507184, compound

Product 1

HCID 69507377HCID 69507377, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of (5-bromo-2-oxo-1,2-dihydroindol-3-ylidene)phenyl-acetic acid (70 mg), 3,4-dimethoxyaniline (63 mg), 4-dimethylaminopyridine (25 mg), benzotriazol-1-yloxy-tris (dimethylamino) phosphonium hexafluorophosphate (BOP, 90 mg) and TEA (1 drop) in DMF (2 mL) was refluxed overnight. The reaction mixture was concentrated and then diluted with aqueous carbonate. The precipitate which formed was washed with dilute HCl and water and then dried to give 16 mg of the title compound.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with aqueous carbonate
  4. customThe precipitate which formed
  5. washwas washed with dilute HCl and water
  6. customdried

Sources & evidence

ORD record
ord-864c963af3b946de9b79364dd71f09a4
Source dataset
uspto-grants-2007_05
Patent number
US07214700B2

Reaction notes

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