tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidine-1-carboxylate

HRID 2378975Notes

Reaction equation

HRID 2378975 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:6]2=[CH:5][C:4]=1[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=1>CO.[Pt](=O)=O>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([Si:12]([CH:13]([CH3:15])[CH3:14])([CH:16]([CH3:18])[CH3:17])[CH:19]([CH3:20])[CH3:21])[C:6]2=[CH:5][C:4]=1[CH:22]1[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH2:26][CH2:27]1

Participants

4

Reactant 1

HCID 59006352tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59006353tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To colorless solution of tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (998 mg, 2.055 mmol) in MeOH (30 mL) was added platinum(IV) oxide (98 mg, 0.432 mmol) at rt. The mixture was shaked on Par Shaker for 3 hr under H2 (55 psi). The mixture was filtered with MeOH (20 mL), concentrated on rotary vacuo to afford the expected product, tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidine-1-carboxylate (995 mg, 100%) as a light grey solid. Mass spec 488.27 Calc for C27H45N3O3Si 487.32, which was pure enough to be used in next reaction.

Workup

  1. filtrationThe mixture was filtered with MeOH (20 mL)
  2. concentrationconcentrated on rotary vacuo

Sources & evidence

ORD record
ord-a2bc4fb18d564a97b671ce6bf0dd3650
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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