Methyl iodide → HCID 9823708, compound

HRID 1453986Notes

Reaction equation

HRID 1453986 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:17]([C:18]#[N:19])=[CH:16][O:15][CH:14]3[C:20]4[C:24](=[CH:25][CH:26]=[C:13]23)[N:23]=[CH:22][CH:21]=4)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].IC.[C:29](=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:17]([C:18]#[N:19])=[CH:16][O:15][C:14]3[C:20]4[CH:21]=[CH:22][N:23]([CH3:29])[C:24]=4[CH:25]=[CH:26][C:13]2=3)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 69001380HCID 69001380, compound

Product 1

HCID 9823708HCID 9823708, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-indolo[4,5-b]pyran (51 mg, 0.124 mmol), iodomethane (23 μL, 0.370 mmol) and cesium carbonate (120 mg, 0.368 mmol) in acetone (2 mL) was stirred at room temperature in a sealed tube. After stirring at room temperature for 2.5 days, the reaction was diluted with EtOAc (20 mL). The insoluble material was filtered, and washed with EtOAc (30 mL). The EtOAc solution were combined, washed with brine (2×5 mL), dried over MgSO4, and evaporated to yield an off-white solid. The crude product was purified by column chromatography (silica gel, EtOAc:hexanes, 1:1) to yield 51 mg (97%) of an off-white solid. 1H NMR (CDCl3): 7.43 (d, J=0.6 Hz, 1H), 7.07 (d, J=3.3 Hz, 1H), 7.05 (dd, J=0.6, 8.4 Hz, 1H), 6.95 (d, J=2.1 Hz, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.58 (dd, J=0.6, 3.3 Hz, 1H), 4.81 (s, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.78 (s, 3H).

Workup

  1. stirringAfter stirring at room temperature for 2.5 days
  2. filtrationThe insoluble material was filtered
  3. washwashed with EtOAc (30 mL)
  4. washwashed with brine (2×5 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto yield an off-white solid
  8. customThe crude product was purified by column chromatography (silica gel, EtOAc:hexanes, 1:1)

Sources & evidence

ORD record
ord-602fb082b36a4fffb19f6bc18e0e7765
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

Loading…