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

HRID 382053Notes

Reaction equation

HRID 382053 reaction equation
[NH2:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[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:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][C:33](Cl)=[O:34]>C([O-])(O)=O.[Na+].C1COCC1>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([C:3]2[C:2]([NH:1][C:33](=[O:34])[CH2:32][C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)=[CH:10][CH:9]=[C:8]3[C:4]=2/[C:5](=[CH:12]/[C:13]2[NH:14][CH:15]=[CH:16][C:17]=2[O:18][CH3:19])/[C:6](=[O:11])[NH:7]3)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 9798339(Z)-5-amino-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 9956403(Z)-N-[2,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamideYield 42.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Using Method M above, (Z)-5-amino-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (28 mg, 0.08 mmol) (from Example 41 supra) was acylated with 2-thiopheneacetyl chloride (25.7 mg, 0.16 mmol) (Aldrich) in saturated aqueous NaHCO3 (0.16 mL) and THF (2 mL) at room temperature for 3 h to give (Z)-N-[2,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-2-thiopheneacetamide (yield: 16 mg, 42%).

Sources & evidence

ORD record
ord-b7043152f5c24c8f8eda75a3def32dab
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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