Methyl iodide → HCID 10384648, compound

HRID 1768461Notes

Reaction equation

HRID 1768461 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][OH:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[CH3:27]I.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][O:26][CH3:27])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10247806HCID 10247806, compound

Product 1

HCID 10384648HCID 10384648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 25 mg (0.07 mmol) of 1-9 in 1 mL of DMF was added a small amount of MeI and NaH (60% suspension in oil) and the mixture was left to stir for 15 h at room temperature. The reaction was quenched with 1 drop of water and loaded directly onto a RP HPLC and eluted with CH3CN/H2O with 0.1% TFA to provide 2-1 as a white solid. Data for 2-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.4 (s, 1H), 4.8 (d, 1H), 4.7 (d, 1H), 4.45 (d, 1H), 4.35 (d, 1H), 3.4 (s, 3H), 2.8 (s, 6H) ppm. HRMS (MS) calc'd M+H for C21H22F2N2O2: 373.1722. Found: 373.1722.

Workup

  1. waitthe mixture was left
  2. customThe reaction was quenched with 1 drop of water
  3. washeluted with CH3CN/H2O with 0.1% TFA

Sources & evidence

ORD record
ord-6a7f8536528b4832a133bbc505f7d72b
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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