2-(Tributylstannyl)pyrimidine → 2-(((2S,3R)-1-(5-Fluoro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

HRID 61170Notes

Reaction equation

HRID 61170 reaction equation
CC1C=CC(C2C=CC=CN=2)=C(C=1)C(OC)=O.Br[C:19]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:20]=1[C:21]([N:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([CH3:29])[C@H:24]1[CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])=[O:22].C([Sn](CCCC)(CCCC)[C:52]1[N:57]=[CH:56][CH:55]=[CH:54][N:53]=1)CCC>>[F:46][C:43]1[CH:44]=[CH:45][C:19]([C:52]2[N:57]=[CH:56][CH:55]=[CH:54][N:53]=2)=[C:20]([CH:42]=1)[C:21]([N:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([CH3:29])[C@H:24]1[CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])=[O:22]

Participants

4

Reactant 3

HCID 27632512-(Tributylstannyl)pyrimidineHCID 67982793Methyl 5-methyl-2-(pyridin-2-yl)benzoateHCID 1177279552-(((2S,3R)-1-(2-Bromo-5-fluorobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 1177279542-(((2S,3R)-1-(5-Fluoro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

Procedure

The title compound was prepared following the same general protocol as described for methyl 5-methyl-2-(pyridin-2-yl)benzoate in Example A9, using 2-(((2S,3R)-1-(2-bromo-5-fluorobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione and 2-(tributylstannyl)pyrimidine. ESI-MS (m/z): 445 [M+1]+.

Sources & evidence

ORD record
ord-8d7850ab5ef84be38842b776d44ab866
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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