6-(Hydroxymethyl)pyridine-3-boronic acid → 2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

HRID 1487453Notes

Reaction equation

HRID 1487453 reaction equation
[Cl:1][CH:2]([Cl:21])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:20])[CH3:19])=[O:4].[OH:22][CH2:23][C:24]1[N:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[Cl:1][CH:2]([Cl:21])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:27]3[CH:28]=[N:29][C:24]([CH2:23][OH:22])=[CH:25][CH:26]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:20])[CH3:19])=[O:4]

Participants

3

Reactant 2

HCID 441182556-(Hydroxymethyl)pyridine-3-boronic acidHCID 86695394(4S,5R)-3-(dichloroacetyl)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyl-1,3-oxazolidine

Product 1

HCID 866954062,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

Procedure

Following the general procedure of Example 1—Step 1 and making non-critical variations but using 2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone and (6-(hydroxymethyl)pyridin-3-yl)boronic acid as starting materials the title compound is obtained (800 mg): m/z (CI) M−H 426.1.

Sources & evidence

ORD record
ord-6b2075fe9d2c49218f7c73871f51afde
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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