HCID 86762621, compound → HCID 86762622, compound

HRID 2409058Notes

Reaction equation

HRID 2409058 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:12]=12)C(=O)OC(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][NH:2][CH2:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[CH:18]=[CH:19][C:12]=12

Participants

4

Reactant 1

HCID 86762621HCID 86762621, compound

Product 1

HCID 86762622HCID 86762622, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl methyl((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)carbamate (232 mg, 0.593 mmol) in DCM (20 mL) and TFA (10 mL) was stirred at RT for 3 h. The reaction mixture was quenched with water (100 mL) and extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to afford 132 mg (76.4%) of N-methyl(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methanamine as a yellow solid. MS (ESI): m/z=292.2 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with DCM (50 mL×3)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f79bbc810d874c5ca817243cfcf9d1bb
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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