Hydrochloric Acid → 2,3-dihydro-1H-pyrrolo(3,4-c)pyridine

HRID 624246Notes

Reaction equation

HRID 624246 reaction equation
Cl.[CH:2]([C:5](C(C)C)([CH:8]([CH3:10])C)[CH2:6][NH2:7])([CH3:4])[CH3:3].[N:14](C1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1)=C=O>CN(C)C=O.O1CCCC1>[CH2:6]1[C:5]2[CH:8]=[CH:10][N:14]=[CH:4][C:2]=2[CH2:3][NH:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 437068HCID 437068, compoundHCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 15194172,3-dihydro-1H-pyrrolo(3,4-c)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

HCl (1.55 g, 8.03 mmol) was suspended in dimethylformamide (30 ml) and treated with triisopropylethylamine (4.21 ml, 24.08 mmol). After stirring for 20 minutes, the mixture was cooled to −15° C. 2-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.028 g, 8.03 mmol) was dissolved in 10 ml tetrahydrofuran and added via syringe over 10 minutes. The mixture was allowed to warm to room temperature, and it was stirred for 3 hours and concentrated under a stream of nitrogen to minimal volume. The residue was diluted with cold water to give a turbid mixture which was filtered with water washes to provide the title compound after drying.

Workup

  1. additionadded via syringe over 10 minutes
  2. temperatureto warm to room temperature
  3. stirringit was stirred for 3 hours
  4. concentrationconcentrated under a stream of nitrogen to minimal volume
  5. additionThe residue was diluted with cold water
  6. customto give a turbid mixture which
  7. filtrationwas filtered with water

Sources & evidence

ORD record
ord-4354085bbccd42b08bc76929c93c6ed7
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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