Sodium Carbonate → HCID 58466261, compound

HRID 335969Notes

Reaction equation

HRID 335969 reaction equation
FC(F)(F)S(O[C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[C:13]([F:32])=[CH:14][C:15]([N:26]4[CH2:30][CH2:29][CH2:28][C:27]4=[O:31])=[CH:16][C:17]=3[C@@:18]32[CH2:24][O:23][C:22]([NH2:25])=[N:21]3)=[CH:9][CH:8]=1)(=O)=O.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[NH2:25][C:22]1[O:23][CH2:24][C@:18]2([N:21]=1)[C:19]1[CH:20]=[C:7]([C:37]3[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=3)[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[C:17]2=[CH:16][C:15]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])=[CH:14][C:13]=1[F:32]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 86658499HCID 86658499, compound

Product 1

HCID 58466261HCID 58466261, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Resealable tube was charged with (S)-2-amino-4′-fluoro-2′-(2-oxopyrolidin-1-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (130 mg, 0.26 mmol), tetrakis(triphenylphosphine)palladium(0) (30.0 mg, 0.026 mmol), pyridin-3-ylboronic acid (51.0 mg, 0.42 mmol). DMF (1.3 mL) and sodium carbonate (2M, 0.4 mL, 0.8 mmol) were added and the mixture was sealed and heated at 90° C. for 2 h. The mixture was partitioned between water (1 mL) and ethyl acetate (5 mL), organic layer was washed with water, concentrated and purified by FC on 12 g RediSep Gold column using 10-80% DCM/MeOH/NH4OH 90:10:1 in DCM. The fractions containing pure product by TLC were combined and concentrated to afford (S)-1-(2-amino-5′-fluoro-2′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)pyrolidin-2-one.

Workup

  1. customthe mixture was sealed
  2. customThe mixture was partitioned between water (1 mL) and ethyl acetate (5 mL), organic layer
  3. washwas washed with water
  4. concentrationconcentrated
  5. custompurified by FC on 12 g RediSep Gold column
  6. additionThe fractions containing pure product by TLC
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-11d54a41ed15477d960ed95d2b11b460
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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