Tetrabutylammonium Fluoride → 1-(2-Chloro-4-fluoro-phenyl)-2-(4-hydroxy-phenyl)-3-methyl-5-piperidin-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 254342Notes

Reaction equation

HRID 254342 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[Cl:31])[C:22]3[CH2:21][CH2:20][N:19]([N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[C:18](=[O:38])[C:17]=3[C:16]=2[CH3:39])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[N:23]1[C:22]2[CH2:21][CH2:20][N:19]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:18](=[O:38])[C:17]=2[C:16]([CH3:39])=[C:15]1[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 668656722-[4-(tert-Butyldimethylsilanyloxy)phenyl]-1-(2-chloro-4-fluorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 166661661-(2-Chloro-4-fluoro-phenyl)-2-(4-hydroxy-phenyl)-3-methyl-5-piperidin-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 30.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(tert-Butyldimethylsilanyloxy)phenyl]-1-(2-chloro-4-fluorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one (0.929 g, 1.63 mmol) was suspended in THF (10 ml) and TBAF (1M in THF, 1.64 ml) was added. The reaction mixture was stirred at rt for 1 h whereafter the solvent was evaporated and ethyl acetate/water added. The phases were separated and the organic phase dried and evaporated. The crude product was recrystallised from ethyl acetate/toluene to yield the product as an orange solid (0.223 g, 23% over 3 steps).

Workup

  1. customwas evaporated
  2. additionethyl acetate/water added
  3. customThe phases were separated
  4. customthe organic phase dried
  5. customevaporated
  6. customThe crude product was recrystallised from ethyl acetate/toluene

Sources & evidence

ORD record
ord-6f12cf801f3149d29d34de352d0bed5d
Source dataset
uspto-grants-2011_01
Patent number
US07875626B2

Reaction notes

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