Selectfluor → ethyl 5-bromo-3-fluoro-1-methyl-1H-indole-2-carboxylate

HRID 1481761Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]2[F:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 5-bromo-1-methyl-1H-indole-2-carboxylate (2.93 g, 10.39 mmol) in MeCN (52 mL) was added Selectfluor® (3.87 g, 10.92 mmol, 1.05 eq) at 0° C. in three portions with an interval of 10 min. The reaction was stirred at 0° C. for 30 min before it was allowed to warm to room temperature then stirred for an additional 30 min. The reaction was monitored by TLC analysis. Once the starting material was completely consumed, the reaction was quenched with sat. NaHCO3 and then extracted by CH2Cl2 (4×25 mL). The solvent was removed to give a crude product which was purified by flash column chromatography (0-10% EtOAc in hexanes) to afford the desired product (860 mg, 2.87 mmol) in 28% yield.

Workup

temperatureto warm to room temperature
stirringthen stirred for an additional 30 min
customOnce the starting material was completely consumed
customthe reaction was quenched with sat. NaHCO3
extractionextracted by CH2Cl2 (4×25 mL)
customThe solvent was removed
customto give a crude product which
customwas purified by flash column chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-38007c0f59ba44cc8e04f73d8ac9666c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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