Sodium hydride → Methyl 4-chloro-1-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 513191Notes

Reaction equation

HRID 513191 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[H-].[Na+].Cl[CH2:18][C:19]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:21][N:20]=1>CN(C=O)C.[NH4+].[Cl-]>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]([CH2:18][C:19]3[N:23]=[C:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[O:21][N:20]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 26599236methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Product 1

HCID 86720571Methyl 4-chloro-1-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylateYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (500 mg, 2.374 mmole) in DMF (10 mL) was added NaH (60% dispersion in mineral oil, 123 mg, 3.09 mmole) portionwise at RT. After 30 min 3-(chloromethyl)-5-phenyl-1,2,4-oxadiazole (601 mg, 3.09 mmole) was added all at once as a solid. After 6 hr the mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, O-20% EtOAc/hexanes) gave the title compound (553 mg, 63%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.21 (d, J=6.0 Hz, 1 H); 8.05 (dd, J=7.8, 1.5 Hz, 2 H); 7.59-7.54 (m, 1 H); 7.54-7.44 (m, 3 H); 7.39-7.35 (m, 1 H); 6.03 (s, 2 H); 3.97 (s, 3 H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1242f06c7b44ff6bc4ccaef8c3a7106
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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