Dimethyl Sulfate → methyl 1H-indole-5-carboxylate

HRID 634085Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

The solution of 1H-indole-5-carboxylic acid (1.0 g, 6.2 mmol, Aldrich) and K2CO3 (0.939 g, 6.8 mmol) in DMF (10 mL) was heated to 65° C., and Me2SO4 (0.78 g, 6.2 mmol) was added dropwise between 65-70° C. over 15 min. The reaction was stirred for 1 h at 80° C. then the mixture was poured into ice/water. The resulting precipitate was collected by filtration and dried in vacuo to give methyl 1H-indole-5-carboxylate (0.91 g, 5.2 mmol, 85.8%). MS (ESI, pos. ion) m/z: 176 (M+1).

Workup

filtrationThe resulting precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-70482e4da5d0428f94c7fd1e39f08510
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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