((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate → ethyl 3-chloro-5-(((1R)-2,2-difluorocyclopropyl)methoxy)pyridine-2-carboxylate

Reaction equation

[Cl:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[N+](C1C=CC(S(O[CH2:27][C@H:28]2[CH2:30][C:29]2([F:32])[F:31])(=O)=O)=CC=1)([O-])=O>>[Cl:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[C:6]([O:8][CH2:27][C@H:28]2[CH2:30][C:29]2([F:32])[F:31])[CH:7]=1

Participants

Reactant 2

HCID 86731320((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate

HCID 86731395Ethyl 3-chloro-5-hydroxypicolinate

Product 1

HCID 86731394ethyl 3-chloro-5-(((1R)-2,2-difluorocyclopropyl)methoxy)pyridine-2-carboxylate

Procedure

Using ethyl 3-chloro-5-hydroxypyridine-2-carboxylate and ((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate, and in the same manner as in Example 5, the title compound was obtained.

Sources & evidence

ORD record: ord-c9dd53e9e4af470ab94ba521e6e77ccf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

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