Potassium Carbonate → methyl 3-iodo-1H-indole-5-carboxylate

HRID 1529362Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].COS(OC)=O>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-Iodo-1H-indole-5-carboxylic acid (8.0 g, 27.68 mmol) in DMF (80 mL) was added potassium carbonate (4.2 g, 30.44 mmol) and heated at 60° C. for 5 min. Dimethylsulphite (3.5 g, 27.68 mmol) was added and the resulting mixture was stirred at 80° C. for 1 h. The reaction mixture was then added ice cold water and extracted with EtOAc (240 mL). The organic layer was dried over Na2SO4, filtered, concentrated to dryness. The crude solid was washed with n-pentane to obtain the title compound (8.0 g, 95%) as a white solid. MS (ESI, pos. ion) m/z: 299.9 (M−1).

Workup

extractionadded ice cold water and extracted with EtOAc (240 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
washThe crude solid was washed with n-pentane

Sources & evidence

ORD record: ord-b459907caabb47b5b3ee8fb027a19b9e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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