Potassium Carbonate → HCID 58466218, compound

HRID 335984Notes

Reaction equation

HRID 335984 reaction equation
[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10](B4OC(C)(C)C(C)(C)O4)=[CH:11][CH:12]=3)[C@@:7]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:6]=2[CH:5]=[C:4]([O:30][CH3:31])[CH:3]=1.Cl[C:33]1[CH:38]=[N:37][CH:36]=[C:35]([C:39]#[C:40][CH3:41])[N:34]=1.C(=O)([O-])[O-].[K+].[K+]>O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:33]4[CH:38]=[N:37][CH:36]=[C:35]([C:39]#[C:40][CH3:41])[N:34]=4)=[CH:11][CH:12]=3)[C@@:7]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:6]=2[CH:5]=[C:4]([O:30][CH3:31])[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 67387140HCID 67387140, compoundHCID 86658506HCID 86658506, compound

Product 1

HCID 58466218HCID 58466218, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Combined tetrakis(triphenylphosphine)palladium (54.2 mg, 0.047 mmol), (S)-4′-fluoro-2′-methoxy-7′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (200 mg, 0.47 mmol, prepared as described in Method BB40) and 2-chloro-6-(prop-1-ynyl)pyrazine (93 mg, 0.61 mmol) in a sealable tube and potassium carbonate (1.5 M) (1.6 mL, 2.35 mmol) was added. The tube was sealed and heated at 110° C. in a microwave for 8 min. The reaction solution was diluted with water and extractd by EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc again. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide a brown oil that was purified by chromatography through a gold Redi-Sep pre-packed silica gel column using a gradient of 25% to 50% to 80% DCM: MeOH: NH4OH (90:10:1) in 40% EtOAc in hexane to provide (S)-4′-fluoro-2′-methoxy-7′-(6-(prop-1-ynyl)pyrazin-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (60 mg, 0.144 mmol, 30.7% yield) as white solid.

Workup

  1. customThe tube was sealed
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc again
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a brown oil that
  9. customwas purified by chromatography through a gold Redi-Sep pre-packed silica gel column

Sources & evidence

ORD record
ord-78a319706805471eb0f09a4269947899
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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