Water → HCID 10187944, compound

HRID 1278828Notes

Reaction equation

HRID 1278828 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Br:7][C:8]1[C:9]([O:31][CH3:32])=[C:10]([NH2:30])[CH:11]=[C:12]([C:14]2[C:26]3[C:25]([CH3:27])=[C:24]([CH3:28])[S:23][C:22]=3[C:21]([Br:29])=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[CH:19]3)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:30][C:10]1[CH:11]=[C:12]([C:14]2[C:26]3[C:25]([CH3:27])=[C:24]([CH3:28])[S:23][C:22]=3[C:21]([Br:29])=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[CH:19]3)[CH:13]=[C:8]([Br:7])[C:9]=1[O:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 10300103HCID 10300103, compound

Product 1

HCID 10187944HCID 10187944, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl bromoacetate (0.285 mL, 3.01 mmol) was added to a stirred, room temperature suspension of 3-bromo-5-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-methoxy-phenylamine (0.260 g, 0.529 mmol) and potassium carbonate (0.411 g, 3.00 mmol) in DMF (1.7 mL). After two days, more methyl bromoacetate (0.135 mL, 1.5 mmol) and the reaction mixture was stirred for a day longer. The reaction mixture was added to water and the solid was filtered and washed with water. The solid was triturated with pet. ether and dried at 60° C. under vacumm to provide the title compound as a white solid (0.212 g, 71%): mp 194-198° C.: NMR (DMSO-d6); 8.17 (dd, J=8, 1 Hz, 1H), 7.63 (ddd, J=8, 6, 1 Hz, 1H), 7.53-7.45 (m, 2H), 6.77 (d, J=2 Hz, 1H), 6.54 (d, J=2 Hz, 1H), 6.10 (t, J=7 Hz, 1H), 3.97 (dd, J=7, 4 Hz, 2H), 3.83 (s, 3H), 3.52 (s, 3H),2.43 (s, 3H), 1.69 (s, 3H); MS (FAB+): 2 bromine isotope pattern 561, 563, 565; Anal. Calc. for C24H21Br2NO3S: C, 51.17, H, 3.76, N, 2.49. Found: C, 50.43, H, 3.63, N, 2.53.

Workup

  1. filtrationthe solid was filtered
  2. washwashed with water
  3. customThe solid was triturated with pet. ether
  4. customdried at 60° C. under vacumm

Sources & evidence

ORD record
ord-0c0fa119e6574f87a2c768f77ab0fde6
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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