Sodium hydride → Ethyl 2-(5-bromo-1-(4-iodobenzyl)-2-methyl-1H-indol-3-yl)acetate

HRID 1721373Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:23][C:22]1[CH:25]=[CH:26][C:19]([I:18])=[CH:20][CH:21]=1)[C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of the product of Step 1 (536.2 mg, 2 mmol) and 4-iodobenzyl chloride (504 mg, 2 mmol) in dry DMF (10 mL) at 0° C. was added sodium hydride (80 mg, 2 mmol, 60% in oil). The mixture was stirred at 20° C. for 20 hours and a saturated NH4Cl solution (10 mL) was added. The mixture was extracted with EtOAc, the extracts were dried over MgSO4 and concentrated to an oil. The oil was purified by flash chromatography on silica gel, eluting with 20% EtOAc in hexane to afford 704 mg (69%) of the title compound. 1H NMR (CDCl3) 1.23 (3H, t, J=7.1 Hz), 2.28 (3H, s), 3.65 (2H, s), 4.12 (2H, q, J=7.1 Hz), 5.19 (2H, s), 6.64 (2H, d, J=8.3 Hz), 6.98 (1H, d, J=8.6 Hz), 7.17 (1H, dd, J=8.6 Hz, 1.8 Hz), 7.56 (2H, d, J=8.3 Hz), 7.68 (1H, d, 1.8 Hz).

Workup

extractionThe mixture was extracted with EtOAc
dry with materialthe extracts were dried over MgSO4
concentrationconcentrated to an oil
customThe oil was purified by flash chromatography on silica gel
washeluting with 20% EtOAc in hexane

Sources & evidence

ORD record: ord-dfa24a348b2c48c7b63dfae5e9bdc2e5
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05510368

Reaction notes

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