Diisopropylethylamine → ethyl 2-(1-acetyl-5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)acetate

HRID 1404089Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH3:9])=[C:6]([Br:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]([CH2:16]/[CH:17]=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=[O:15])[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:13]([N:12]1[C:3]2[C:2](=[C:7]([O:8][CH3:9])[C:6]([Br:10])=[CH:5][C:4]=2[F:11])[C:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16]1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 8-7 (20 g, 44.0 mmol) in anhydrous DMF (250 mL) was added Pd(OAc)2 (2.0 g, 8.8 mmol), Bu4NBr (14.3 g, 44.0 mmol) and DIPEA (14.2 g, 110 mmol) under N2. The mixture was stirred at 80° C. for 3 h. TLC showed that the reaction was completed. The mixture was poured into ice water and extracted with ethyl acetate (150 mL×3). The organic layers were combined and were concentrated in vacuo. The residue was purified by flash chromatography (Silica-gel, petroleum ether/ethyl acetate=10:1) to afford 8-8 (13.0 g, 79%) as a white solid.

Workup

extractionextracted with ethyl acetate (150 mL×3)
concentrationwere concentrated in vacuo
customThe residue was purified by flash chromatography (Silica-gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record: ord-d372ba9c457242758dd574ed08edbc0c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912220B2

Reaction notes

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