p-Anisoyl chloride → HCID 59971442, compound

HRID 382035Notes

Reaction equation

HRID 382035 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2/[C:11](=[CH:19]/[C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)/[C:12](=[O:18])[NH:13]3)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[CH3:32][O:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>C(Cl)(Cl)Cl>[O:18]=[C:12]1[NH:13][C:14]2[C:10](/[C:11]/1=[CH:19]/[C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)=[C:9]([C:5]1[CH:4]=[C:3]([NH:2][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)[CH:8]=[CH:7][CH:6]=1)[CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 9819192HCID 9819192, compound

Product 1

HCID 59971442HCID 59971442, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of (Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one hydrochloride (30 mg, 0.089 mmol) (from Example 5 supra) and Et3N (24 μL , 0.172 mmol) in 3 mL of chloroform was cooled to −70° C. and then treated with 4-methoxybenzoyl chloride (17.4 mg, 0.102 mmol) (Fluka). The reaction mixture was stirred at −70° C. for 1 hr and then stirred at room temperature for 15 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50% ethyl acetate-hexanes elution) provided pure (Z)-N-[3-[2,3-dihydro-2-oxo3-[(1H-pyrrol-2-yl) methylene]-1H-indol-4-yl]-phenyl]-4-methoxybenzamide (31 mg, 80%) as a brown solid (mp 209-211° C.).

Workup

  1. stirringstirred at room temperature for 15 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, 50% ethyl acetate-hexanes elution)

Sources & evidence

ORD record
ord-8e1070f0d0ec402e9bb2c6a86b40b61f
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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