5-Bromo-4-methyl-2-(oxolan-3-yloxy)pyridine → Rac-[1-(3,4-dichloro-phenyl)-2-[4-methyl-6-(tetrahydro-furan-3-yloxy)-pyridin-3-yl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 384920Notes

Reaction equation

HRID 384920 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:9](=[O:14])N(OC)C)([CH3:4])([CH3:3])[CH3:2].Br[C:25]1[C:26]([CH3:37])=[CH:27][C:28]([O:31][CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[N:29][CH:30]=1>>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:9]([C:25]1[CH:30]=[N:29][C:28]([O:31][CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[CH:27][C:26]=1[CH3:37])=[O:14])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 684099505-Bromo-4-methyl-2-(oxolan-3-yloxy)pyridine2×HCID 87442373Rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester2×

Product 1

HCID 68410141Rac-[1-(3,4-dichloro-phenyl)-2-[4-methyl-6-(tetrahydro-furan-3-yloxy)-pyridin-3-yl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (Intermediate 9) and rac-5-bromo-4-methyl-2-(tetrahydro-furan-3-yloxy)-pyridine (Intermediate 22) in analogy to Example 1a): MS (ISN): 479.0 and 481.0 (M−H)−.

Sources & evidence

ORD record
ord-bd5084ac703149b7b00be64303302bab
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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