Dimethylformamide → HCID 69311233, compound

HRID 2222584Notes

Reaction equation

HRID 2222584 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:11][N:12](C=O)[CH3:13].[OH:16]N1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CC(O)=O>[NH:6]1[C:11]2=[N:12][CH:13]=[C:10]([CH2:9][C:8]([NH2:7])=[O:16])[CH:2]=[C:3]2[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 880121H-Indazol-5-amine

Product 1

HCID 69311233HCID 69311233, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a solution of 5-aminoazaindole (0.6 g, 4.5 mmol) in dry DMF (11 mL) N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (TBTU, 1.45 g, 9 mmol), 1-hydroxybenzotriazole (HOBt, 0.69 g, 9 mmol) and glacial AcOH (260 micro), diisopropylethylamine (DIPEA, 3.12 mL, 18 mmol) was slowly dropped in ca. 30′ under stirring. The reaction mixture was stirred at room temperature for 18 h, concentrated and the residue was purified by flash chromatography eluting with dichloromethane/MeOH 10:1. The desired 1H-pyrrolo[2,3-b]pyridin-5-ylacetamide (title compound) was obtained in 95% yield (0.78 g, 4.2 mmol).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with dichloromethane/MeOH 10:1

Sources & evidence

ORD record
ord-96ec231f5a0d46fbb706c2b18e5e006e
Source dataset
uspto-grants-2008_05
Patent number
US07371862B2

Reaction notes

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