Triethylamine → ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate

HRID 1189559Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:16]1([C:22](=O)[CH:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][C:25](=O)[CH3:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C.C(Cl)Cl>[CH3:26][C:25]1[N:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-aminoacetate hydrochloride (0.548 g, 3.92 mmol) was diluted with Ethanol (10 ml) then charged with triethylamine (0.746 ml, 5.35 mmol) and 1,2-diphenylpentane-1,4-dione (0.900 g, 3.57 mmol), added as a solution in DCM. The reaction was heated at 100° C. overnight, after which TLC showed a new spot (less polar, Rf˜0.9 in 20% EtOAc/hexanes). The reaction was diluted with 10 mL DCM and washed with water (10 mL). The aqueous layer was back-extracted with DCM (10 mL×2). The organics were combined, dried, filtered, and concentrated to yield a crude orange oil. This oil was loaded on a SiO2 column and purified using a 0-20% gradient of EtOAc in hexanes, affording ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate (0.780 g, 2.442 mmol, 68.5% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.37-7.33 (m, 3H), 7.27-7.24 (m, 2H), 7.16-7.11 (m, 4H), 7.07-7.04 (m, 1H), 6.24 (b, 1H), 4.42 (s, 2H), 4.21 (q, 2H), 2.27 (s, 3H), 1.25 (t, 3H).

Workup

washwashed with water (10 mL)
extractionThe aqueous layer was back-extracted with DCM (10 mL×2)
customdried
filtrationfiltered
concentrationconcentrated
customto yield a crude orange oil
custompurified

Sources & evidence

ORD record: ord-551c65679f1547be9657f27eb20e1ba3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674115B2

Reaction notes

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