Trifluoroacetic acid → (3-Chloro-benzyl)-[5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-methyl-1H-pyrazol-3-yl]-amine

HRID 509993Notes

Reaction equation

HRID 509993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=3)[N:17]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=2)O)[N:10]([CH3:12])[N:11]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[N:10]([CH3:12])[N:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58259270[5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-fluoro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Product 1

HCID 58259317(3-Chloro-benzyl)-[5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-methyl-1H-pyrazol-3-yl]-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-fluoro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (147, 0.070 g, 0.13 mmol) in 4 mL of dichloromethane, triethylsilane (0.210 mL, 1.31 mmol) and trifluoroacetic acid (0.100 mL, 1.30 mmol) were added and the reaction stirred overnight at room temperature. The reaction was concentrated under vacuum, then ethyl acetate was added, then washed with 1M aqueous potassium carbonate, then brine. The organic layer was dried over sodium sulfate, filtered and the filtrate purified by silica gel flash column chromatography eluting with a gradient of 2-20% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum and the resulting solid washed with ethyl acetate in hexane to provide the desired compound.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. additionethyl acetate was added
  3. washwashed with 1M aqueous potassium carbonate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate purified by silica gel flash column chromatography
  7. washeluting with a gradient of 2-20% methanol in dichloromethane
  8. concentrationconcentrated under vacuum
  9. washthe resulting solid washed with ethyl acetate in hexane

Sources & evidence

ORD record
ord-baa395babd2f4493b93d3f45cf193865
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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