2-Thiopheneacetyl chloride → (Z)-N-[2,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide

HRID 382067Notes

Reaction equation

HRID 382067 reaction equation
[NH2:1][C:2]1[C:3]([C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[CH:25][NH:26]3)=[CH:22][CH:21]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35](Cl)=[O:36].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[NH:26]1[C:27]2[C:23](=[CH:22][CH:21]=[C:20]([C:3]3[C:2]([NH:1][C:35](=[O:36])[CH2:34][C:30]4[S:29][CH:33]=[CH:32][CH:31]=4)=[CH:10][CH:9]=[C:8]4[C:4]=3/[C:5](=[CH:12]/[C:13]3[NH:14][CH:15]=[CH:16][C:17]=3[O:18][CH3:19])/[C:6](=[O:11])[NH:7]4)[CH:28]=2)[CH:24]=[CH:25]1

Participants

6

Reactant 3

HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 18363862(Z)-5-amino-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 9913671(Z)-N-[2,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-5-amino-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (22 mg, 0.059 mmol) (from Step B above) in 2 mL tetrahydrofuran was added 2-thiopheneacetyl chloride (20 mg, 0.12 mmol) (Aldrich) and a saturated aqueous solution of sodium bicarbonate (0.15 mL). The reaction was stirred at room temperature for 16 hours at which time the reaction was diluted with water (10 mL), and the THF was evaporated in vacuo. The product was then extracted with EtOAc, and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The resulting powder was recrystallized from EtOAc/Hex to give product as yellow crystals. (Yield 19 mg, 66%).

Workup

  1. customthe THF was evaporated in vacuo
  2. extractionThe product was then extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting powder was recrystallized from EtOAc/Hex
  6. customto give product as yellow crystals

Sources & evidence

ORD record
ord-f72c4870e2ba4c2ba00fdf019d4101a5
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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