Methyl iodide → HCID 71625034, compound

HRID 589609Notes

Reaction equation

HRID 589609 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[NH:11][C:10]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]([CH3:25])[C:10]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71625155HCID 71625155, compound

Product 1

HCID 71625034HCID 71625034, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 7 (200 mg, 0.6 mmol) was added in portions to a mixture of sodium hydride (60 mg, 1.2 mmol) in DMF (5 mL) at 0° C. After 15 min, methyl iodide (50 μL, 0.9 mmol) was added and the mixture was stirred for 1 h. The reaction was allowed to warm to rt and stirred overnight under N2. The reaction mixture was then quenched with ice water and extracted with EtOAc. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 50% EtOAc-hexanes to provide 166 mg (63%) of product 4 as an off white solid, mp 110-111° C. 1H NMR (300 MHz, DMSO-d6) δ 2.35 (s, 3H), 3.83 (s, 3H), 4.00 (s, 3H), 7.06 (d, J=9 Hz, 2H), 7.23-7.29 (m, 4H), 7.63 (d, J=9 Hz, 1H). LC-MS (CI): m/z 346.1 [(M+H)+ C18H16ClNO2S requires 345.06]. Purity (100%). Calcd for C18H16ClNO2S: C, 62.51; H, 4.66; N, 4.05; S, 9.27; Cl, 10.25. Found: C, 62.79; H, 4.64; N, 3.98; S, 9.05; Cl, 10.03.

Workup

  1. stirringstirred overnight under N2
  2. customThe reaction mixture was then quenched with ice water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography
  7. washeluting with a linear gradient

Sources & evidence

ORD record
ord-d4e89c2a52b54d7085a19830e114288c
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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