Nitrogen → HCID 86730164, compound

HRID 1850128Notes

Reaction equation

HRID 1850128 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([C:18]2[N:23]=[C:22]([N:24]3[C@@H:28]([CH:29]([CH3:31])[CH3:30])[CH2:27][O:26][C:25]3=[O:32])[CH:21]=[CH:20][N:19]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH3:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1.C(=O)(O)[O-].[Na+].N#N>O1CCOCC1.CCOC(C)=O>[CH:29]([C@H:28]1[CH2:27][O:26][C:25](=[O:32])[N:24]1[C:22]1[CH:21]=[CH:20][N:19]=[C:18]([N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:37]3[CH:36]=[N:35][N:34]([CH3:33])[CH:38]=3)=[CH:3][CH:4]=2)[CH3:9])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:23]=1)([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 947NitrogenHCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86730162HCID 86730162, compound

Product 1

HCID 86730164HCID 86730164, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 5 mL microwave vial a solution of tert-butyl (S)-1-(4-bromophenyl)ethyl(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)carbamate (101 mg, 0.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.24 mmol), Sodium bicarbonate (0.2 mL, 0.4 mmol, 2 M aqueous solution) in Dioxane (2 mL) was bubbled N2 for 3 min then Cl2Pd(dppf)CH2Cl2 (16 mg, 0.02 mmol) was added. The capped tube was heated to 100° C. for 16 h. After cooling the reaction mixture was diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to give a white solid (50 mg, 49.3% yield).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwashed with water (10 mL)
  3. customAfter separation
  4. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  5. dry with materialCombined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%)

Sources & evidence

ORD record
ord-a7fdc6ba5bad491eab20acc1712deadc
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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