Methyl chloroformate → Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 392088Notes

Reaction equation

HRID 392088 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N+:8]=2[O-])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C[Si](C)(C)N[Si](C)(C)C.[Cl:25]C(OC)=O>C1COCC1>[Cl:25][C:7]1[N:8]=[C:9]2[C:4]([CH:3]=[C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:1]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 13838HexamethyldisilazaneHCID 178468513HCID 178468513, compound

Product 1

HCID 21868758Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethyl 7-azaindole-2-carboxylate-7-oxide (1.32 g, 6.4 mmol) and hexamethyldisilazane (1.4 mL, 6.6 mmol) in THF (30 mL) at 0° C. was added dropwise over 30 min a solution of methyl chloroformate (12 mL, 15.5 mmol) in THF (5 mL). The mixture was warmed to room temperature, stirred for 2 h and partitioned between ether (50 mL) and water (50 mL). The aqueous layer was extracted with ether (30 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate) and purified by column chromatography [SiO2; heptane—ether (3:1)1 to give ethyl 6-chloro-7-azaindole-2-carboxylate as a white solid (0.38 g, 26%). mp 144-145° C. Found: C, 53.69; H, 4.05; N, 12.39%. C10H9N2ClO2 requires: C, 53.47; H, 4.04; N, 12.46%.

Workup

  1. custompartitioned between ether (50 mL) and water (50 mL)
  2. extractionThe aqueous layer was extracted with ether (30 mL)
  3. washThe combined organic extracts were washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. custompurified by column chromatography [SiO2

Sources & evidence

ORD record
ord-e07c05bd3b2047a991854b1e48279b5d
Source dataset
uspto-grants-2004_10
Patent number
US06800627B1

Reaction notes

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