Methyl iodide → HCID 71269001, compound

HRID 1429368Notes

Reaction equation

HRID 1429368 reaction equation
[CH2:1]([C@@H:8]1[C:15](=[O:16])[NH:14][CH2:13][C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[CH2:10][N:9]1[S:21]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2)(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:36]I>C1COCC1.O>[CH2:1]([C@@H:8]1[C:15](=[O:16])[N:14]([CH3:36])[CH2:13][C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[CH2:10][N:9]1[S:21]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2)(=[O:22])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71269635HCID 71269635, compound

Product 1

HCID 71269001HCID 71269001, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8 (50 mg, 0.11 mmol) in THF (3 mL) at −10° C. was slowly added NaH (5.2 mg, 0.12 mmol). The mixture was warmed to rt and stirred for 1 h. To it was added CH3I (50 mg, 0.33 mmol). The reaction mixture was stirred at rt for 16 h, diluted with H2O (10 mL) and extracted with EA (2×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give 9 (50 mg, 96% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 9.14-9.11 (m, 1H), 8.24-8.19 (m, 2H), 7.92 (d, J=8.0 Hz, 1H), 7.59-7.54 (m, 1H), 7.44-7.36 (m, 3H), 7.22-7.13 (m, 5H), 7.08-7.04 (m, 1H), 6.72 (d, J=7.2 Hz, 1H), 5.80-5.76 (m, 1H), 5.43-5.30 (m, 2H), 4.20 (d, J=16.8 Hz, 1H), 3.46-3.30 (m, 2H), 3.06-3.00 (m, 1H), 2.75 (s, 3H); MS (ESI+) m/z: 472 [M+H]+.

Workup

  1. customat −10° C.
  2. stirringThe reaction mixture was stirred at rt for 16 h
  3. extractionextracted with EA (2×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by Prep-TLC

Sources & evidence

ORD record
ord-cdd295b265b045169f65ca1b0f4fcf43
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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