Acetyl chloride → HCID 178474719, compound

HRID 1069708Notes

Reaction equation

HRID 1069708 reaction equation
[CH2:1]([NH:4][C:5](=[O:7])[CH3:6])[C:2]#[CH:3].C(N)C#C.C(Cl)(=O)C.[F:16][C:17]1[C:18](I)=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])/[C:20]/2=[CH:27]\[C:28]1[NH:32][CH:31]=[N:30][C:29]=1[CH3:33]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.CCN(CC)CC>[F:16][C:17]1[C:18]([C:3]#[C:2][CH2:1][NH:4][C:5](=[O:7])[CH3:6])=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[CH:27][C:28]1[NH:32][CH:31]=[N:30][C:29]=1[CH3:33]

Participants

9

Reactant 4

HCID 6367Acetyl chlorideHCID 239041PropargylamineHCID 24079665881-41-6HCID 178433242HCID 178433242, compound2×

Product 1

HCID 178474719HCID 178474719, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

Using Method C above, N-propargylacetamide (32.8 mg, 0.34 mmol) (prepared by the reaction of propargyl amine (Aldrich) with acetyl chloride and triethyl amine in dichloromethane at 0° C. for 3 h) was coupled with (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (Starting Material 3 supra) (50 mg, 0.135 mmol) using (Ph3P)4Pd (16 mg) and Cul (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 80° C. for 5 h to give N-[3-[2,3-dihydro-5-fluoro-3-[(5-methyl-3H-imidazol-4-yl)methylene]-2-oxo-1H-indol-4-yl]-prop-2-ynyl]-acetamide. (Yield 35 mg, 77%).

Sources & evidence

ORD record
ord-024f38fa088c42d9b4de7fb1d8a33538
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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