5-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde → HCID 86682009, compound

HRID 1749825Notes

Reaction equation

HRID 1749825 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N: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.[Br:26][C:27]1[CH:28]=[C:29]2[C:35]([CH:36]=O)=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1>CO.N1CCCCC1>[Br:26][C:27]1[CH:28]=[C:29]2[C:35](/[CH:36]=[C:7]3\[O:8][C:4]4[C:3]([CH2:12][N:13]5[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]5)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=4[C:6]\3=[O:9])=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1

Participants

5

Reactant 2

HCID 247296055-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehydeHCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 86682009HCID 86682009, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.020 g, 0.058 mmol) obtained in Example A16, Step 1 in methanol (1.0 mL) was added with 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.010 g, 0.044 mmol). Then, the mixture was added with 5 drops of piperidine, and the mixture was stirred at 50° C. for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was suspended in methylene chloride and thereby washed to obtain tert-butyl (Z)-4-({2-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.018 g, 56%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed

Sources & evidence

ORD record
ord-1789a219910a4adda8086e76739d98c3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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