3,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one → (4R)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-fluoro-N,N-dimethy l-L-prolinamide

HRID 1662596Notes

Reaction equation

HRID 1662596 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.[F:28][C@H:29]1[CH2:33][NH:32][C@H:31]([C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:30]1>>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:12])[C:2]2([N:32]1[CH2:33][C@H:29]([F:28])[CH2:30][C@H:31]1[C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20]

Participants

3

Reactant 2

HCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-oneHCID 67428691HCID 67428691, compound

Product 1

HCID 67430074(4R)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-fluoro-N,N-dimethy l-L-prolinamide

Procedure

With 3.78 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and the compound obtained in Step 6-3 (13.5 mmol) as starting materials, respectively 2.06 g (Isomer A: colorless powder) and 2.74 g (Isomer B: colorless powder) of two species of diastereoisomers of the title compound were obtained by a similar method to Step 4-2.

Sources & evidence

ORD record
ord-812f89b7cc4544b8bd322bc7cb910765
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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