Methanol → 4-(2-tert-butyl-1-methyl-1H-imidazol-4-yl)-1H-pyrrolo[2,3-b]pyridine, trifluoroacetate salt

HRID 44917Notes

Reaction equation

HRID 44917 reaction equation
[C:1]([C:5]1[N:6]([CH3:27])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[N:16](OCC[Si](C)(C)C)[C:17](C)=[CH:18][C:11]=23)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29].CO.[NH4+].[OH-]>>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[C:1]([C:5]1[N:6]([CH3:27])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][CH:17]=[CH:18][C:11]=23)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 66597115HCID 66597115, compound

Product 1

HCID 672934414-(2-tert-butyl-1-methyl-1H-imidazol-4-yl)-1H-pyrrolo[2,3-b]pyridine, trifluoroacetate saltYield 94%

Procedure

A solution of 4-(2-tert-butyl-1-methyl-1H-imidazol-4-yl)-1-[2-(trimethylsilyl)-ethoxy]-methyl-1H-pyrrolo[2,3-b]pyridine (0.010 g, 0.000026 mol) in TFA (3 mL, 0.04 mol) was stirred for 2 hours. Then the excess TFA was evaporated and the residue was stirred in methanol (3 mL, 0.07 mol) and NH4OH (1 mL) for 16 hours. The solvents were removed and the product was purified by preparative-HPLC (C18 eluting with a gradient of ACN/H2O containing 0.1% TFA) to afford 4-(2-tert-butyl-1-methyl-1H-imidazol-4-yl)-1H-pyrrolo[2,3-b]pyridine, trifluoroacetate salt (9 mg, 90%).

Workup

  1. customThen the excess TFA was evaporated
  2. customThe solvents were removed
  3. customthe product was purified by preparative-HPLC (
  4. washC18 eluting with a gradient of ACN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-24c7787e041648cf96ce03346e904bc3
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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