Hydrochloric Acid → HCID 178422233, compound

HRID 1445924Notes

Reaction equation

HRID 1445924 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:17]C)=[C:11]2[CH:10]=[C:9]1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].Cl>CN(C=O)C>[CH2:1]([N:8]1[C:12]2[N:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 588959911-Benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178422233HCID 178422233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 6 (0.45 g, 1.78 mmol) in anhydrous DMF (10 mL) was added NaSMe (0.37 g, 5.35 mmol) under N2. The reaction mixture was stirred at 80° C. for 45 min. After cooling, the mixture was poured into a saturated solution of NH4Cl (20 mL), and 1 N HCl (3-4 mL) was added until pH 4-5. The resultant mixture was extracted with EtOAc (5×30 mL), the combined organic extracts were washed with H2O (2×10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was chromatographed on a silica gel column using 5% methanol in CH2Cl2 as eluent to give 7 as an amorphous white solid. Yield: 0.30 g, 70%; ESI MS: m/z 238.9 (M+1).

Workup

  1. temperatureAfter cooling
  2. additionwas added until pH 4-5
  3. extractionThe resultant mixture was extracted with EtOAc (5×30 mL)
  4. washthe combined organic extracts were washed with H2O (2×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-d86457b16a4849009c5d3363c8b397c4
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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