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

HRID 2039858ノート

反応式

HRID 2039858 の反応式
[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

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3070da145ed3418988131c2998c45f95
出典データセット
uspto-grants-2013_11
特許番号
US08580813B2

反応ノート

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