Methyl iodide → HCID 18453545, compound

HRID 1271408Notes

Reaction equation

HRID 1271408 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[CH2:13][CH:12]1[C:14]1[NH:18][N:17]=[N:16][N:15]=1.I[CH3:20].[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[CH2:13][CH:12]1[C:14]1[N:18]=[N:17][N:16]([CH3:20])[N:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178517018HCID 178517018, compound

Product 1

HCID 18453545HCID 18453545, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension containing 5′-bromo-2-(tetrazole-5-yl)-spiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-one (153 mg, 0.5 mmol), iodomethane (85 mg, 0.6 mmol) and sodium hydroxide (20 mg, 0.5 mmol) in 5 mL of DMF was stirred at room temperature for 16 hours. The reaction mixture was concentrated to dryness in vacuo. The solid residue was chromatographed using hexane and ethyl acetate (v/v 1:1) as eluent. The chromatographed material gave the title compound in 34% yield (55 mg). MS m/z 320 [M+1]+. 1H NMR (CDCl3): δ 8.52 (s, 1H), 7.27 (m, 1H), 7.04 (br, 1H), 6.80 (m, 1H), 4.34 (s, 3H), 3.35 (t, 1H), 2.48 (m, 1H), 2.05 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. customThe solid residue was chromatographed

Sources & evidence

ORD record
ord-cc143af8bc1d4788aecb4a8a8c829a1e
Source dataset
uspto-grants-2007_04
Patent number
US07205328B2

Reaction notes

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