tert-Butanol → HCID 67357244, compound

Temperature

0 °C

A mixture of diphenylphosphoryl azide (4.3 g, 16 mmol), Et3N (7.3 ml, 52 mmol) and 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3B, 2.8 g, 10 mmol) in DMF (30 ml) was stirred at 0° C. for 1 h. The mixture was extracted with EtOAc/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was dissolved in toluene (30 ml) and added 2-methylpropan-2-ol (3.9 g, 52 mmol). The mixture was stirred at 70° C. for 2 h. The mixture was concentrated in vacuo and purified by chromatography (SiO2, hexanes:EtOAc=1:1) to give tert-butyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (3C, 340 mg, 0.99 mmol, 9.5% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (t, J=7.20 Hz, 3H) 1.49 (s, 9H) 4.14 (q, J=7.33 Hz, 2H) 7.60 (s, 1H) 7.83 (d, J=0.76 Hz, 1H) 8.36 (d, J=0.76 Hz, 1H) 9.59 (s, 1H).

1. extractionThe mixture was extracted with EtOAc/H2O
2. washThe organic layer was washed with brine
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. dissolutionThe crude mixture was dissolved in toluene (30 ml)
6. stirringThe mixture was stirred at 70° C. for 2 h
7. concentrationThe mixture was concentrated in vacuo
8. custompurified by chromatography (SiO2, hexanes:EtOAc=1:1)

ORD record

ord-a719868312ca4b47b686ffc22d1a0a7c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802695B2