Selectfluor → (S)-ethyl 2-(2-bromo-4-fluoro-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879265Notes

Reaction equation

HRID 879265 reaction equation
[Br:1][C:2]1[S:3][C:4]2[C:10]([OH:11])=[C:9]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([CH3:23])=[CH:7][C:5]=2[N:6]=1.[B-](F)(F)(F)[F:25].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[Br:1][C:2]1[S:3][C:4]2[C:10]([OH:11])=[C:9]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([CH3:23])=[C:7]([F:25])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 71003373(S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 71003370(S)-ethyl 2-(2-bromo-4-fluoro-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction mixture of (S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (75A) (380 mg, 0.948 mmol), Selectfluor (1.9 g, 4.74 mmol) in acetonitrile (7 mL) was reacted at 0° C. for 5 days. The reaction mixture was washed by 1.5 M KH2PO4, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-40% EtOAc in hexanes to give 75B (137 mg, 35%). LCMS-ESI+: calc'd for C16H19FNO4S: 420.0 (M+H+). Found: 420.1 (M+H+).

Workup

  1. customwas reacted at 0° C. for 5 days
  2. washThe reaction mixture was washed by 1.5 M KH2PO4
  3. extractionextracted by EtOAc
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-a2d30d786f0a4616b04732edfe1eee94
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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