Dimethylformamide → HCID 10108919, compound

HRID 428707Notes

Reaction equation

HRID 428707 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:9]1\[C:10](=[O:29])[NH:11][C:12]2[C:17]\1=[C:16]([C:18]#[C:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[C:15]([N+:26]([O-])=O)=[CH:14][CH:13]=2.[NH4+].[Cl-].CN(C=O)C>O.CO.[Zn]>[NH2:26][C:15]1[C:16]([C:18]#[C:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:29])/[C:9]/2=[CH:8]\[C:4]1[NH:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 10293504HCID 10293504, compound

Product 1

HCID 10108919HCID 10108919, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Using Method L above, (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-4-[(3-pyridinyl)ethynyl]-2H-indol-2-one (0.1 g, 0.26 mmol) (from Example 68 above) was reduced with Zn (0.15 g, 2.33 mmol) and NH4Cl (30.6 mg, 0.57 mmol) in 10% water in methanol (10 mL) with a trace of DMF and heating at 90° C. for 5 h, to yield (Z)-5-amino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-[(3-pyridinyl)ethynyl]-2H-indol-2-one. (Yield 28 mg, 30%).

Sources & evidence

ORD record
ord-cfca4c70c23f4030a249147c118a0973
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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