Cesium carbonate → HCID 86640730, compound

HRID 1970351Notes

Reaction equation

HRID 1970351 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([O:25][CH3:26])([CH3:24])[CH3:23])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:27])=[CH:10][CH:11]=3)[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:34][C:35]([F:50])([C:46]([F:49])([F:48])[F:47])[C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[S:38](F)(=[O:40])=[O:39]>CN(C=O)C>[F:43][C:37]([F:42])([S:38]([O:27][C:9]1[CH:8]=[C:7]2[C@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:6]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([O:25][CH3:26])([CH3:24])[CH3:23])[CH:18]=3)[O:13][C:12]2=[CH:11][CH:10]=1)(=[O:40])=[O:39])[C:36]([F:44])([F:45])[C:35]([F:50])([F:34])[C:46]([F:49])([F:48])[F:47]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 67246263HCID 67246263, compound

Product 1

HCID 86640730HCID 86640730, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25-mL flask was charged with (R)-2′-amino-3-(3-methoxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (577.53 mg, 1.581 mmol), cesium carbonate (566 mg, 1.739 mmol), and DMF (7903 μL). The resulting mixture was stirred for 10 min, then the vial was submerged in an ice-bath for 10 min. nonafluorobutanesulfonyl fluoride (306 μL, 1.739 mmol) was added dropwise over 2 minutes. Stirred for 2 hours before the mixture was quenched with saturated aqueous ammonium chloride (10 mL). The mixture was partitioned between water (15 mL) and EtOAc (15 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (15 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on an 80-g Redi-Sep column, eluting with 0-50% of a 90:10 mixture of DCM/MeOH in DCM to give (R)-2′-amino-3-(3-methoxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate as a white solid.

Workup

  1. waitthe vial was submerged in an ice-bath for 10 min.
  2. stirringStirred for 2 hours before the mixture
  3. customwas quenched with saturated aqueous ammonium chloride (10 mL)
  4. customThe mixture was partitioned between water (15 mL) and EtOAc (15 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (15 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by chromatography on an 80-g Redi-Sep column
  12. washeluting with 0-50% of a 90:10 mixture of DCM/MeOH in DCM

Sources & evidence

ORD record
ord-8d7533c23d104d10b3d9fc22380a41db
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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