Isopropyl iodide → Ethyl 3-[3-chloro-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

HRID 423359Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[CH:17]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:37](I)([CH3:39])[CH3:38].CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH:37]([CH3:39])[CH3:38])=[C:18]([Cl:23])[CH:17]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To ethyl 3-{3-chloro-5-[5-(3-chloro-4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl}propanoate (D108) (180 mg, 0.40 mmol) and K2CO3 (138 mg, 1.0 mmol) in dry DMF (5 ml) was added isopropyl iodide (85 mg, 0.50 mmol) and the mixture stirred at 80° C. for 30 minutes. Cooled mixture and added EtOAc (50 ml). Washed with water (2×50 ml) and dried over MgSO4. Evaporated off the solvent and crystallised from ethanol to yield the title compound as 120 mg of white solid. δH (400 MHz, d6-DMSO) 1.12 (3H, t), 1.37 (6H, d), 2.91 (2H, t), 4.02 (2H, q), 4.50 (2H, t), 4.89-4.98 (1H, m), 7.72-7.85 (5H, m), 7.95-8.00 (1H, m), 8.24 (1H, d). MS (ES) C24H2335Cl2N3O4 requires 487; found 488 (MH+).

Workup

temperatureCooled mixture
washWashed with water (2×50 ml)
dry with materialdried over MgSO4
customEvaporated off the solvent
customcrystallised from ethanol

Sources & evidence

ORD record: ord-0d1bec91476e47469dae42986d8b1d08
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101775B2

Reaction notes

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