Sodium Bicarbonate → HCID 86713170, compound

HRID 1500283Notes

Reaction equation

[F:1][CH:2]([F:29])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:28])[CH3:27])=[O:4].Br[C:31]1[CH:32]=[CH:33][C:34]([CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])=[N:35][CH:36]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(O)(C)C>[F:1][CH:2]([F:29])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:13]=[CH:14][C:15]([C:31]3[CH:36]=[N:35][C:34]([CH2:37][S:38]([CH3:41])(=[O:39])=[O:40])=[CH:33][CH:32]=3)=[CH:16][CH:17]=2)[O:7][C:6]1([CH3:28])[CH3:27])=[O:4]

Participants

Conditions

Temperature: 120 °C

Procedure

2,2-difluoro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-3-yl)ethanone (100 mg, 0.24 mmol) in 1:1 toluene/isopropyl alcohol (4 mL) is treated with commercially available 5-bromo-2-(methylsulfonylmethyl)pyridine (60 mg, 0.24 mmol), sodium bicarbonate (1 mL of a 2M solution), and (1,1′-bis[diphenylphosphino]ferrocene)dichloropalladium (II) (10 mg, 0.012 mmol) then heated at 120° C. in a microwave for 30 minutes. The mixture is concentrated and purified by column chromatography on silica gel eluting with a gradient of ethyl acetate in heptane to give the title compound (135 mg). m/z (Cl) 457 [M+H].

Workup

concentrationThe mixture is concentrated
custompurified by column chromatography on silica gel eluting with a gradient of ethyl acetate in heptane

Sources & evidence

ORD record: ord-89760c6993984a73bb1beb0ba622cf56
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206126B2

Reaction notes

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