6-Azaindole → tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 1747273Notes

Reaction equation

HRID 1747273 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>CO>[NH:1]1[C:9]2=[CH:8][N:7]=[CH:6][CH:5]=[C:4]2[C:3]([C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 92196-AzaindoleHCID 14797Potassium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 59559369tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

6-Azaindole (4.48 g, 37.9 mmol) was dissolved in MeOH (70 mL) and KOH (4.68 g, 83.4 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (8.31 g, 41.7 mmol) were added. The reaction mixture was heated at 70° C. for 18 h. The residue was partitioned between water (250 mL) and DCM (250 mL) and the aq phase was extracted with DCM (2×250 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow foam (11.3 g, 99%). LCMS (ES+): 300.1 [MH]+.

Workup

  1. customThe residue was partitioned between water (250 mL) and DCM (250 mL)
  2. extractionthe aq phase was extracted with DCM (2×250 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fda56318b14412cac296251b3aed593
Source dataset
uspto-grants-2015_10
Patent number
US09150574B2

Reaction notes

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