Methyl iodide → [3-(1,2-Dimethyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466758Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[S:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:22][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>CN(C=O)C.C1COCC1>[CH3:22][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([S:11][C:12]2[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)=[C:2]1[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

[3-(2-Methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid (0.050 g, 0.17 mmol) was dissolved in DMF:THF (1:1, 4 mL) and cooled to 0° C. Lithium bis(trimethylsilyl)amide solution (0.370 mL, 0.37 mmol, 1.0M in hexanes) was added. After 5 minutes iodomethane (11 μL, 0.18 mmol) was added and the reaction was allowed to warm to room temperature. The reaction was stirred for an additional 5 minutes then submitted to aqueous workup. Purification by preparatory HPLC (10-100% ACN in H2O) provided the title compound.

Workup

temperatureto warm to room temperature
customPurification by preparatory HPLC (10-100% ACN in H2O)

Sources & evidence

ORD record: ord-6b45b39a41f44ec1bfdea5d4ecf857b9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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