Methyl iodide → HCID 24991912, compound

HRID 222479Notes

Reaction equation

HRID 222479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[C:13](=[O:29])[NH:14][C:15](=[O:28])[C:16]=1[C:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][OH:27])=[CH:25][C:20]=2[O:19][CH:18]=1.[H-].[Na+].[CH3:32]I>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[C:13](=[O:29])[N:14]([CH3:32])[C:15](=[O:28])[C:16]=1[C:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][OH:27])=[CH:25][C:20]=2[O:19][CH:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44582642HCID 44582642, compound

Product 1

HCID 24991912HCID 24991912, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-fluoro-1-methyl-1H-indol-3-yl)-4-(6-hydroxymethyl-benzofuran-3-yl)-pyrrole-2,5-dione (0.035 g, 0.090 mmol) in dry THF was added sodium hydride (0.005 g, 0.011 mmol, 55% in mineral oil) and methyliodide (0.006 mL, 0.090 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with ice water, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, evaporated in vacuo and purified by preparative TLC (methanol:dichloromethane; 5:95) to afford the product (0.012 g, 34%) as an orange solid. 1H NMR (CDCl3, 400 MHz) 3.19 (s, 3H), 3.86 (s, 3H), 4.71 (s, 2H), 6.62 (dd, J=2.3, 10.0 Hz, 1H), 6.83-6.90 (m, 3H), 7.21 (dd, J=4.3, 8.9 Hz, 1H), 7.51 (s, 1H), 7.81 (s, 1H), 8.11 (s, 1H), 13C NMR (CDCl3, 100 MHz) 23.9, 33.4, 64.8, 104.7, 106.5, 106.8, 109.6, 110.0, 110.1, 110.6, 110.8, 111.3, 121.4, 121.7, 122.1, 124.5, 126.1, 126.2, 130.8, 133.2, 134.4, 137.8, 147.0, 154.8, 156.6, 158.9, 170.9, 171.3.

Workup

  1. customThe reaction was quenched with ice water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated in vacuo
  5. custompurified by preparative TLC (methanol:dichloromethane; 5:95)

Sources & evidence

ORD record
ord-cd7aea4eee60482bb1a25f1228e8dad0
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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