(Z)-Prop-1-en-1-ylboronic acid → HCID 178439564, compound

HRID 2069998Notes

Reaction equation

HRID 2069998 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)=[CH:21]/[CH3:22]>>[C:14]1([C@@H:12]([N:8]2[C:6]3=[N:7][C:2](/[CH:20]=[CH:21]\[CH3:22])=[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 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 178461678HCID 178461678, compound

Product 1

HCID 178439564HCID 178439564, compoundYield 63%

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), (Z)-prop-1-enyl boronic acid (2.0 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 2 N 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 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 (63%) as an off-white foam. LCMS m/z (APCI)=281.1 (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 2 N K2CO3 (4.2 volume equivalents) by syringe
  7. temperatureThe mixture was cooled to room temperature
  8. additiondiluted with 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-516e81b870cf40daaa53269648abe5df
Source dataset
uspto-grants-2012_10
Patent number
US08299248B2

Reaction notes

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