Trifluoroacetic acid → [5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine

HRID 510003Notes

Reaction equation

HRID 510003 reaction equation
C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:26]2[C:34]3[C:29](=[N:30][CH:31]=[C:32]([Br:35])[CH:33]=3)[NH:28][CH:27]=2)OC)=[CH:19][N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Br:35][C:32]1[CH:33]=[C:34]2[C:26]([CH2:23][C:20]3[CH:21]=[CH:22][C:17]([NH:7][CH2:8][C:9]4[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=4)=[N:18][CH:19]=3)=[CH:27][NH:28][C:29]2=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58259147{5-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methoxy-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 67200583[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amineYield 61.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To {5-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methoxy-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (154, 0.35 g, 0.63 mmol) in 20.0 mL of acetonitrile, triethylsilane (1.0 mL, 6.3 mmol) and trifluoroacetic acid (0.50 mL, 6.5 mmol) were added and the reaction stirred at 80° C. for 4 hours. The reaction was concentrated under vacuum and combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-2017, 165.1 mg). MS (ESI) [M+H+]+=423.8, 425.8

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. filtrationThe organic layer was filtered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0eb8d695fe8341f799b1e602275e9e08
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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