Methanol → (5-Bromo-3-(tert-butylamino)quinoxalin-2-yl)methanol

HRID 1056168Notes

Reaction equation

HRID 1056168 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]([CH:12]=[O:13])=[N:7]2.[Na].CO.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]([CH2:12][OH:13])=[N:7]2

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 5360545Sodium3×HCID 897823205-Bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde

Product 1

HCID 89784130(5-Bromo-3-(tert-butylamino)quinoxalin-2-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5-bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde (306a) (113 mg, 0.37 mmol) and sodium triacetoxyhydroborate (78 mg, 0.37 mmol) in THF (7.5 mL) was stirred at 25° C. for 10 min. MeOH (1.0 mL) was added, and the resulting mixture was stirred at 25° C. for 10 min. Additional sodium triacetoxyhydroborate (78 mg, 0.37 mmol) was added, and the resulting mixture was stirred at 25° C. for 10 min. Further sodium triacetoxyhydroborate (78 mg, 0.37 mmol) was added, and the resulting mixture was stirred at 25° C. for 10 min. Saturated aq. NaHCO3 (10 mL) was then added, and the resulting mixture was partitioned between EtOAc (70 mL) and half-saturated aq. NaHCO3 solution (50 mL). The organic layer was separated, and the aq. layer was extracted with EtOAc (30 mL). The combined organic extracts were washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated in vacuo to provide (5-bromo-3-(tert-butylamino)quinoxalin-2-yl)methanol (114 mg, 0.37 mmol, 100% yield) as a yellow-brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (1H, d, J=7.6 Hz), 7.76 (1H, d, J=8.0 Hz), 7.20 (1H, t, J=7.9 Hz), 5.10 (1H, br. s.), 4.72 (2H, s), 3.92 (1H, br. s.), 1.62 (9H, s). m/z (ESI, +ve) 310.0/312.0 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 10 min
  2. stirringthe resulting mixture was stirred at 25° C. for 10 min
  3. customthe resulting mixture was partitioned between EtOAc (70 mL) and half-saturated aq. NaHCO3 solution (50 mL)
  4. customThe organic layer was separated
  5. extractionthe aq. layer was extracted with EtOAc (30 mL)
  6. washThe combined organic extracts were washed with brine (40 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cda8f9aae42d4b5fb8720dcc97af2396
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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