Vinylboronic acid → HCID 178437084, compound

HRID 1019716Notes

Reaction equation

HRID 1019716 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9]([OH:11])=[N:10][C:5]2=[N:4][CH:3]=1.[CH:20](B(O)O)=[CH2:21]>>[C:14]1([C@@H:12]([N:8]2[C:6]3=[N:7][C:2]([CH:20]=[CH2:21])=[CH:3][N:4]=[C:5]3[N:10]=[C:9]2[OH:11])[CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 4683185Vinylboronic acidHCID 178461678HCID 178461678, compound

Product 1

HCID 178437084HCID 178437084, compoundYield 54%

Conditions

Temperature
90 °C

Procedure

A scintillation vial equipped with a stirbar was charged with (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), vinyl boronic acid (2.2 equiv), and (DPPF)PdCl2 (0.10 equiv). The vial was fitted with a septum-lined cap and purged with nitrogen for 5-10 min. To this mixture was added dioxane (16.6 volume equivalents) and degassed 2N K2CO3 (4.2 volume equivalents) by syringe. The resulting mixture was heated to 90° C. overnight. The mixture was cooled to room temperature, diluted with 12 volume equivalents EtOAc, washed with twice with saturated aq. NaHCO3, and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound as an off-white solid (54%). LCMS m/z (APCI)=267.0 (M+H).

Workup

  1. customA scintillation vial equipped with a stirbar
  2. customThe vial was fitted with a septum-lined
  3. customcap
  4. custompurged with nitrogen for 5-10 min
  5. additionTo this mixture was added dioxane (16.6 volume equivalents)
  6. customdegassed 2N K2CO3 (4.2 volume equivalents) by syringe
  7. temperatureThe mixture was cooled to room temperature
  8. additiondiluted with 12 volume equivalents EtOAc
  9. washwashed with twice with saturated aq. NaHCO3
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c93b94abecb499e9cd27670886d312f
Source dataset
uspto-grants-2014_05
Patent number
US08716291B2

Reaction notes

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