Methanol → HCID 58318809, compound

HRID 2401514Notes

Reaction equation

HRID 2401514 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH:14][C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1.I[CH3:22].CO>C1COCC1>[F:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[N:14]([CH3:22])[C:15]1[CH:20]=[N:19][CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 58318729HCID 58318729, compound

Product 1

HCID 58318809HCID 58318809, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (110 mg, 4.58 mmol, 1.10 eq) was dissolved in THF (10 mL), added to dry, argon purged flask, and cooled to 0° C. Compound 19 (1.0 g, 4.0 mmol, 1.0 eq) was dissolved in THF (10 mL) and added to sodium hydride solution. The reaction stirred at 0° C. for 30 minutes. Iodomethane (630 mg, 4.44 mmol, 1.10 eq) was added. The reaction warmed to rt and stirred overnight. Methanol was added and the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel afforded 600 mg (57%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 1H), 8.26 (s, 2H), 7.99 (dd, J=7.8, 2.0 Hz, 1H), 7.93 (ddd, J=8.5, 4.8, 2.2 Hz, 1H), 7.51 (dd, J=10.8, 8.7 Hz, 1H), 3.86 (s, 3H), 3.35 (s, 3H); ES-MS [M+1]+:262.1.

Workup

  1. additionadded
  2. customto dry
  3. temperatureThe reaction warmed to rt
  4. stirringstirred overnight
  5. concentrationthe mixture was concentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-951f1ff5fef74963aab08d3e52737436
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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