Triethylamine → HCID 59564624, compound

HRID 2096259Notes

Reaction equation

HRID 2096259 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[N:18]1([CH2:27][C:28](O)=[O:29])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=[CH:19]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:28](=[O:29])[CH2:27][N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=[CH:19]2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22139374(1H-Pyrrolo[2,3-b]pyridin-1-yl)acetic acidHCID 595644911-[2-Bromo-4-(trifluoromethyl)phenyl]piperazine

Product 1

HCID 59564624HCID 59564624, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-Bromo-4-trifluoromethyl-phenyl)-piperazine (225 mg, 0.73 mmol), pyrrolo[2,3-b]pyridin-1-yl-acetic acid (154 mg, 0.87 mmol), TBTU (304 mg, 0.95 mmol) and triethylamine (304 μl, 2.18 mmol) are combined in dichloromethane (3 mL). The resulting reaction is allowed to stir at ambient temperature for 2 h. Water is added and the mixture is extracted with EtOAc. The organic layer is washed with water, brine, dried (Na2SO4) and concentrated. The crude product is purified using biotage chromatography eluting with 0-50% EtOAc/hexane. Removal of the solvent provides 1-[4-(2-bromo-4-trifluoromethyl-phenyl)-piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-yl-ethanone as a colorless foam (268 mg, 79%).

Workup

  1. customThe resulting reaction
  2. extractionthe mixture is extracted with EtOAc
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product is purified
  7. washeluting with 0-50% EtOAc/hexane
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-957a2c0af2d342ac8445f7d91e9ff6b9
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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