2-(Tributylstannyl)pyrazine → HCID 67382669, compound

HRID 335855Notes

Reaction equation

HRID 335855 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:30])=[CH:9][C:10]([O:28][CH3:29])=[CH:11][C:12]=3[C:13]32[CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:16]3)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[N:40][CH:39]=[CH:38][N:37]=1)CCC>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.CN(C=O)C>[F:30][C:8]1[C:7]2[O:6][C:5]3[C:14](=[CH:15][C:2]([C:36]4[CH:41]=[N:40][CH:39]=[CH:38][N:37]=4)=[CH:3][CH:4]=3)[C:13]3([CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:16]3)[C:12]=2[CH:11]=[C:10]([O:28][CH3:29])[CH:9]=1

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 67383557HCID 67383557, compound

Product 1

HCID 67382669HCID 67382669, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A 10 ml resealable tube was charged with tert-butyl 7′-bromo-4′-fluoro-2′-methoxy-5H-spiro[thiazole-4,9′-xanthene]-2-ylcarbamate (300 mg, 0.606 mmol), tetrakis(triphenylphosphine)palladium (70.0 mg, 0.061 mmol) and DMF (3.03 ml) and 2-(tributylstannyl)pyrazine (402 mg, 1.090 mmol). The mixture was stirred for 3 hr at 110° C. The mixture was partitioned between EtOAc and water. The organic layer was washed twice with water, filtered through celite and concentrated under reduced pressure. The solids were triturated with hexane to remove excess tin residue before being filtered. Purification by silica gel chromatography (10-80% CH2Cl2/MeOH/NH4OH in CH2Cl2) to provide tert-butyl 4′-fluoro-2′-methoxy-7′-(pyrazin-2-yl)-5H-spiro[thiazole-4,9′-xanthene]-2-ylcarbamate.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed twice with water
  3. filtrationfiltered through celite and
  4. concentrationconcentrated under reduced pressure
  5. customThe solids were triturated with hexane
  6. customto remove excess tin residue
  7. filtrationbefore being filtered
  8. customPurification by silica gel chromatography (10-80% CH2Cl2/MeOH/NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-9a11ced67d9b41aab0bc2cb3ce4a2767
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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