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

HRID 983176Notes

Reaction equation

HRID 983176 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(C)=[CH:22][C:23]=2[C:24](O)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.[CH2:28](Cl)[CH2:29]Cl.[CH:32]1[CH:33]=[CH:34][C:35]2[N:40](O)N=[N:38][C:36]=2C=1>CN(C=O)C.C(Cl)Cl>[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:28]([CH3:29])=[CH:22][C:23]=2[C:24]([N:40]2[CH2:32][CH2:33][CH2:34][C@@H:35]2[CH2:36][N:38]2[CH2:6][CH2:7][C@H:2]([F:1])[CH2:3]2)=[O:25])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

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

Product 1

HCID 600615794-(3-Fluoro phenyl)-3-[1-{3-[(r)-2-((s)-3-fluoro-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.28 mmol), EDC (120 mg, 0.63 mmol), HOBt (40 mg, 0.3 mmol) in DMF (4 mL) was added TEA (0.15 mL) and (S)-3-fluoro-1-(R)-1-pyrrolidin-2-ylmethyl-pyrrolidine (95 mg, 0.55 mmol). The mixture was stirred at rt for 20 hours. The reaction was diluted with DCM, washed with water, NaHCO3, dried and concentrated. The residue was purified on a silica gel column to give the titled compound.

Workup

  1. washwashed with water, NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-fd61c62f83d14187980d861846ed422f
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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