Hydrochloric Acid → 1H-Pyrrolo[3,2-b]pyridine, 2,3-dihydro-3,3-dimethyl-6-(phenylmethyl)-

HRID 1475418Notes

Reaction equation

HRID 1475418 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([CH3:25])([CH3:24])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C(OCC)C>CO.C(Cl)Cl>[CH2:17]([C:14]1[CH:15]=[C:16]2[NH:8][CH2:9][C:10]([CH3:25])([CH3:24])[C:11]2=[N:12][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 70981129HCID 70981129, compound

Product 1

HCID 709801961H-Pyrrolo[3,2-b]pyridine, 2,3-dihydro-3,3-dimethyl-6-(phenylmethyl)-Yield 102.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6-Benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester (1.66 g, 4.9 mmol) was dissolved in methanol (16 mL) and placed under a nitrogen atmosphere. 4M HCl in 1,4-dioxane (18.5 mL, 74 mmol) was added and the reaction was stirred at room temperature overnight. The reaction was concentrated in vacuo giving a sticky gum. The residue was stripped down from diethyl ether (2×30 mL) giving a sticky solid. The solid was dissolved in DCM (25 mL) and concentrated, to give the title compound (1.2 g), MS: [M+H]+=239.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customgiving a sticky gum
  3. customgiving a sticky solid
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-857f54e98e5b4a96b1f535acc6278b32
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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