Ethyl Acetate → HCID 10134266, compound

HRID 966539Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][C:12]=1[CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C(O[CH2:32][CH3:33])(=O)C>CCC(C)=O>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:11][CH2:12][N:13]3[CH2:33][CH2:32][CH2:15][CH2:14]3)[CH:18]=2)[NH:13][C:12]=1[CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester (5.0 g, 17.8 mmol), K2CO3 (6.14 g, 44.4 mmol), KI (0.029 g, 1.78 mmol) and N(chloroethyl)cyclopentyl hydrochloride (3.02 g, 17.8 mmol) were mixed together in MEK (100 mL) and refluxed at 80° C. for 72 hours. The reaction was then permitted to cool and diluted with ethyl acetate. Then solution was washed with deionized water and brine, dried on Na2SO4, filtered and concentrated under reduced pressure. The resulting crude mixture was then chromatographed (10% MeOH/CH2Cl2) to give 1.20 g (26.8%) of the desired ester as a white solid, mp 110-116° C. 1HNMR (400 MHz, DMSO): δ 1.64 (b,4H), 2.45 (b, 4H), 2.59 (s, 3H, ArCH3), 4.00 (m, 2H), 5.27 (s, 2H), 6.70 (dd, J=8.54 Hz, J=2.44 Hz, 1H), 7.15 (d, J=8.79 Hz, 1H), 7.28-7.47 (m, 5H), 11.71 (s, NH); MS(APCI+) m/z 379.1(MH+). Anal. Calcd for C23H26N2O3.0.42H2O: C, 71.56;H, 7.01; N, 7.26. Found: C, 71.36: H, 6.93: N, 7.04; IR(KBr): 3371, 2909, 1665, 1481, 1448, 1178, 1087 cm−1.

Workup

temperatureto cool
washThen solution was washed with deionized water and brine
customdried on Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting crude mixture was then chromatographed (10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-09bf4bfa119f4013b4ab4b33205cb379
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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