Sodium Bicarbonate → HCID 86713199, compound

HRID 1500311Notes

Reaction equation

HRID 1500311 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:6][CH:7]=1.[F:20][CH:21]([F:48])[C:22]([N:24]1[C@H:28]([CH2:29][F:30])[C@@H:27]([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)[O:26][C:25]1([CH3:47])[CH3:46])=[O:23].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:48][CH:21]([F:20])[C:22]([N:24]1[C@H:28]([CH2:29][F:30])[C@@H:27]([C:31]2[CH:36]=[CH:35][C:34]([C:2]3[CH:3]=[CH:4][C:5]([C:8](=[O:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:6][CH:7]=3)=[CH:33][CH:32]=2)[O:26][C:25]1([CH3:46])[CH3:47])=[O:23]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 866954142,2-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)ethanoneHCID 86713198HCID 86713198, compound

Product 1

HCID 86713199HCID 86713199, compoundYield 34.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of the product of step 2, Example 28 (1 g, 3 mmol) and the product of step 4, Example 8 (1.26 g, 3 mmol) in toluene 20 ml and isopropyl alcohol (20 mL) is treated with sodium hydrogen carbonate saturate solution (10 ml). The mixture is deoxygenated and PdCl2(dppf) (111 mg, 0.15 mmol) is added and the reaction mixture deoxygenated again. The mixture is heated at 75° C. overnight. The reaction mixture is partitioned between ethyl acetate (100 ml) and water (50 ml). The phases were separated, the aqueous extracted with ethylacetate and the combined organic layers evaporated. Column chromatography (0-50% ethyl acetate in heptane) gave the title compound (554 mg). MS (ESI+) m/z 536.0 [M+H].

Workup

  1. concentrationsaturate solution (10 ml)
  2. customThe mixture is deoxygenated
  3. customthe reaction mixture deoxygenated again
  4. customThe reaction mixture is partitioned between ethyl acetate (100 ml) and water (50 ml)
  5. customThe phases were separated
  6. extractionthe aqueous extracted with ethylacetate
  7. customthe combined organic layers evaporated

Sources & evidence

ORD record
ord-96e72c683df64d699e14bdb9b362e0c7
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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