Water → [5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

HRID 2261562Notes

Reaction equation

HRID 2261562 reaction equation
C(OC(=O)[N:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([Br:33])[CH:31]=3)[NH:26][CH:25]=2)O)=[CH:18][N:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>C(#N)C>[Br:33][C:30]1[CH:31]=[C:32]2[C:24]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([NH:7][CH2:8][C:9]4[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=4)=[N:17][CH:18]=3)=[CH:25][NH:26][C:27]2=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593354(5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 59593278[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To {5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl}-(4-chloro-benzyl)-carbamic acid tert-butyl ester (45, 180.0 mg, 0.33 mmol) in acetonitrile (30.0 mL) were added trifluoroacetic acid (2.0 mL, 0.026 mol) and triethylsilane (4.0 mL, 0.025 mol). The reaction was heated to reflux for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give compound (P-0038, 120 mg, 85.2%). MS (ESI)[M+H+]+=427.2, 429.2.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 10% methanol in dichloromethane
  9. customto give compound (P-0038, 120 mg, 85.2%)

Sources & evidence

ORD record
ord-bc126e62187348e7a2fcf9c2769195f8
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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