Hydrochloric Acid → HCID 86672696, compound

HRID 2168484Notes

Reaction equation

HRID 2168484 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7]([CH2:15][CH:16](OC)[O:17]C)[CH:6]=[C:5]2[CH3:21].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7]([CH2:15][CH:16]=[O:17])[CH:6]=[C:5]2[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66898628HCID 66898628, compound

Product 1

HCID 86672696HCID 86672696, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 5-chloro-1-(2,2-dimethoxyethyl)-3-methyl-1H-indole-7-carboxylate (909 mg, 2.9 mmol) from Step C above in THF (20 ml) was added 2N HCl (20 ml). The mixture was heated to 60° C. for 4 h. The solvent was evaporated and the residue purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate) to afford methyl 5-chloro-3-methyl-1-(2-oxoethyl)-1H-indole-7-carboxylate (690 mg, 89%) as a yellow solid: MS (ESI+) m/z 266 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a8efb98aa8084568ac0ab66f7101e369
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

Loading…