HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1721373
Notes
Print preview

Reaction equation

HRID 1721373 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8172111-(Chloromethyl)-4-iodobenzeneHCID 10780239Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 22414955Ethyl 2-(5-bromo-1-(4-iodobenzyl)-2-methyl-1H-indol-3-yl)acetateYield 69%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe extracts were dried over MgSO4
  3. concentrationconcentrated to an oil
  4. customThe oil was purified by flash chromatography on silica gel
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes