tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate → (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylmethanamine

HRID 2409046Notes

Reaction equation

HRID 2409046 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:18][C:5]2=[N:6][C:7]=1[CH2:8][N:9](C)[C:10](=O)OC(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[CH:19]=[CH:18][C:5]2=[N:6][C:7]=1[CH2:8][NH:9][CH3:10]

Participants

4

Reactant 1

HCID 86762619tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate

Product 1

HCID 86762620(6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylmethanamineYield 77.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-Pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate (200 mg, 0.5 mmol) in CH2Cl2 (5 mL) and TFA (0.5 mL) was stirred at RT for 2 h. The reaction mixture was cooled to 0° C. and then quenched by adding a sat'd. aq. NaHCO3 until the pH was about 8. The mixture was extracted with EtOAc (20 mL×2), and the combined extracts dried (MgSO4), filtered and concentrated under reduced pressure to afford 120 mg (70%) of (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylmethanamine as a brown oil. MS (ESI): m/z=310.3 [M+1]+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched
  3. additionby adding a sat'd
  4. extractionThe mixture was extracted with EtOAc (20 mL×2)
  5. dry with materialthe combined extracts dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f6099debdd244ff977d4efdb28da32c
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

Loading…