1,2-Dichloroethane → 4-(3-Fluoro-phenyl)-3-[1-[5-methyl-3-(4-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 983175Notes

Reaction equation

HRID 983175 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:20][C:21]([CH3:27])=[CH:22][C:23]=2[C:24](O)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.[N:28]1([CH2:33][C@@H:34]2[CH2:39][CH2:38]CN[CH2:35]2)[CH2:32][CH2:31][CH2:30][CH2:29]1.C1C=CC2N(O)N=[N:46][C:44]=2C=1.C(Cl)CCl>C1COCC1.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:20][C:21]([CH3:27])=[CH:22][C:23]=2[C:24]([N:46]2[CH2:44][CH2:35][CH:34]([CH2:33][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH2:39][CH2:38]2)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 697405872-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z) ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 600615294-(3-Fluoro-phenyl)-3-[1-[5-methyl-3-(4-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 70%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3-Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (108 mg, 0.3 mmol) was coupled with (R)-3-pyrrolidin-1-ylmethyl-piperidine (99 mg, 2 eq.), HOBt (1 eq.), EDC (1.5 eq.) and TEA (3 drops) in THF (1 mL), acetonitrile (1 mL) at rt for overnight to give 107 mg (70%) of the titled compound as a yellow solid.

Sources & evidence

ORD record
ord-b6c8d1eb72d94a7d8e47cb5319a6a12b
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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