Hydrochloric Acid → [1-Phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone

HRID 2039858Notes

Reaction equation

HRID 2039858 reaction equation
[Br-].CC([Zn+])C1C=CC=CC=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.Cl.Cl.Cl.[C:32]1([N:38]2[C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[C:40]([C:47]([N:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)=[O:48])=[C:39]2[CH:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH3:56])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:32]1([N:38]2[C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[C:40]([C:47]([N:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)=[O:48])=[C:39]2[CH:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH3:56])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66922091[1-phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochlorideHCID 178462437HCID 178462437, compound

Product 1

HCID 56661689[1-Phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of example 1, step 5, (120 mg, 27 μmol), α-methylbenzylzinc bromide (820 μl, 408 μmol, 0.5 M in THF), tri(tert-butyl)phosphonium tetrafluoroborate (15.6 mg, 54 μmol) and bis(dibenzylideneacetone)palladium (15.6 mg, 27 μmol) in THF (5 ml) was stirred for 12 h at 80° C. The reaction mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The intermediate was purified by preparative HPLC and reacted analogously as described in example 1, step 7. The obtained solid was dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight to give 20 mg of the title compound in the form of the [1-phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochloride.

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe intermediate was purified by preparative HPLC
  6. customreacted analogously
  7. dissolutionThe obtained solid was dissolved in a small quantity of MOH

Sources & evidence

ORD record
ord-3070da145ed3418988131c2998c45f95
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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