3,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one → 3-[(2S)-2-(azetidin-1-ylcarbonyl)-4-fluoropyrrolidin-1-yl]-5-chloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

HRID 1662600Notes

Reaction equation

HRID 1662600 reaction equation
Cl[C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].FC(F)(F)C(O)=O.[N:28]1([C:32]([C@@H:34]2[CH2:38][CH:37]([F:39])[CH2:36][NH:35]2)=[O:33])[CH2:31][CH2:30][CH2:29]1>>[N:28]1([C:32]([C@@H:34]2[CH2:38][CH:37]([F:39])[CH2:36][N:35]2[C:2]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=3)[NH:4][C:3]2=[O:12])=[O:33])[CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-oneHCID 67428608(2S)-2-(azetidin-1-ylcarbonyl)-4-fluoropyrrolidine trifluoroacetate

Product 1

HCID 674299353-[(2S)-2-(azetidin-1-ylcarbonyl)-4-fluoropyrrolidin-1-yl]-5-chloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Procedure

With 2.37 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and the compound obtained in Step 10-3 (3.82 g, crude form) as starting materials, respectively 874 mg (Isomer A: colorless solid) and 1.45 g (Isomer B: colorless amorphous) of two species of diastereoisomers of the title compound were obtained by a similar method to Step 4-2.

Sources & evidence

ORD record
ord-ae527a44c8194f2dbb5874ac0f5fd515
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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