Ammonium Chloride → 7-dibutoxymethyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine

HRID 1932288Notes

Reaction equation

HRID 1932288 reaction equation
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[CH2:7]([O:11][CH:12]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:8][CH2:9][CH3:10].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([O:11][CH:12]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:13]1[N:14]=[CH:15][CH:16]=[C:17]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:19][C:18]=12)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 671410012-Dibutoxymethyl-3-nitropyridineHCID 178448414HCID 178448414, compound

Product 1

HCID 671409247-dibutoxymethyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridineYield 65.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 243 ml, 121 mmol) was slowly added at −78° C. to a solution of 2-dibutoxymethyl-3-nitropyridine (11.53 g, 40 mmol) prepared in Step 2 in tetrahydrofuran (100 ml). The reaction mixture was stirred overnight and a saturated ammonium chloride solution (50 ml) was added thereto. The reaction mixture was diluted with ethyl acetate (100 ml), washed with water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 8 g of the titled compound as brown oil. The product was used in the subsequent step without further purification.

Workup

  1. washwashed with water
  2. dry with materialdried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13111c55a3454774891320f6ac197bc5
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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