Sodium borohydride → HCID 58009987, compound

HRID 1628055Notes

Reaction equation

HRID 1628055 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH:21]=[O:22])[N:20]=[C:15]2[CH:14]=1.[BH4-].[Na+]>O1CCOCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][OH:22])[N:20]=[C:15]2[CH:14]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58382343HCID 58382343, compound

Product 1

HCID 58009987HCID 58009987, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (5.03 g, 11.5 mmol, prepared using D from Preparation #C.1. with (E)-styrylboronic acid and E) in 1,4-dioxane (65 mL) and EtOH (13 mL) was treated with NaBH4 (0.436 g, 11.5 mmol) then stirred overnight at rt. The reaction mixture was concentrated under reduced pressure then the residue was partitioned between EtOAc (125 mL) and saturated aqueous NaHCO3 (100 mL). The layers were separated then the aqueous layer was extracted with EtOAc (75 mL). The combined organic layers were extracted with brine (50 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on neutral alumina with 8:2 DCM/EtOAc then 7:3 DCM/EtOAc then finally EtOAc to give (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (3.19 g, 63%): LC/MS (Table 2, Method a) Rt=2.76 min; MS m/z 439 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc (125 mL) and saturated aqueous NaHCO3 (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (75 mL)
  5. extractionThe combined organic layers were extracted with brine (50 mL)
  6. dry with materialthen dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe material was purified by flash chromatography on neutral alumina with 8:2 DCM/EtOAc

Sources & evidence

ORD record
ord-76a0eee697fc4c2ab7630bad94597cbe
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…