Potassium Hydroxide → HCID 10120008, compound

HRID 1069245Notes

Reaction equation

HRID 1069245 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:33])[CH2:6][NH:7][C:8]1[CH:13]=[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:11]=[C:10]([Br:30])[C:9]=1[O:31][CH3:32]>C1COCC1.CO>[Br:30][C:10]1[C:9]([O:31][CH3:32])=[C:8]([NH:7][CH2:6][C:5]([OH:33])=[O:4])[CH:13]=[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:11]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10187944HCID 10187944, compound

Product 1

HCID 10120008HCID 10120008, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous potassium hydroxide (1N, 0.64 mL, 0.64 mmol) was added to a stirred room temperature solution of [3-bromo-5-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-methoxy-phenylamino]-acetic acid methyl ester (0.180 g, 0.320 mmol) in THF (2.5 mL), methanol (1.5 mL). After 4 h, the solvent was removed and water was added. The suspension was acidified and extracted with ether. Silica gel was added. The ether was removed and the adsorbate was flash chromatographed (Gradient: 7:3pet. ether: ethyl acetate to ethyl acetate to 9:1 ethyl acetate:methanol) to provide the title compound as a white solid (0.112 g, 64%): mp >190° C. (dec): NMR (DMSO-d6); 8.16 (d, J=8 Hz, 1H), 7.63 (ddd, J=8, 6, 1 Hz, 1H), 7.56 (d, J=8 Hz, 1H), 7.48 (ddd, J=8, 6, 1 Hz, 1H), 6.72 (d, J=2 Hz, 1H), 6.43 (d, J=2 Hz, 1H), 5.74 broad s, 1H), 3.83 (s, 3H), 3.46 (s, 2H), 2.42 (s, 3H), 1.71 (s, 3H); MS (FAB+): 2 bromine isotope pattern 547, 549, 551; Anal. Calc. for C23H19Br2NO3S: C, 50.29; H, 3.49; N, 2.55. Found: C, 49.54; H, 3.73; N, 2.26.

Workup

  1. customthe solvent was removed
  2. additionwater was added
  3. extractionextracted with ether
  4. additionSilica gel was added
  5. customThe ether was removed
  6. customchromatographed (Gradient: 7:3pet. ether: ethyl acetate to ethyl acetate to 9:1 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-eb51484ec3fe4ff9b19726a1b18943d1
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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