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

HRID 384913Notes

Reaction equation

HRID 384913 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])=[N:27][C:28]([O:31][CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[CH: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[C:26]([CH3:37])=[N:27][C:28]([O:31][CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[CH:29][CH:30]=1)=[O:14])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 684093293-Bromo-2-methyl-6-((tetrahydrofuran-3-yl)oxy)pyridine2×HCID 87442373Rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester2×

Product 1

HCID 68410380Rac-[1-(3,4-dichloro-phenyl)-2-[2-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-3-bromo-2-methyl-6-(tetrahydro-furan-3-yloxy)-pyridine (Intermediate 13) in analogy to Example 1a): MS (ISP): 481.2 (M+H)+ and 483.2 ((M-Boc)+H)+ (100%).

Sources & evidence

ORD record
ord-ee1d9f95040d4a51bf0436a440a9bfbf
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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