Methyl iodide → HCID 86618265, compound

HRID 1159869Notes

Reaction equation

HRID 1159869 reaction equation
[F:1][C:2]1[C:3]([OH:22])=[C:4]([CH:20]=[O:21])[C:5]2[CH:6]=[CH:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.[C:23]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.C(Cl)Cl>[F:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([CH:20]=[O:21])[C:5]2[CH:6]=[CH:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86618263HCID 86618263, compound2×

Product 1

HCID 86618265HCID 86618265, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

Crude 6-fluoro-5-hydroxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (85 mg, 266 μmol; Intermediate 96) was suspended in acetone (5 mL) and treated with K2CO3 (73.6 mg, 532 μmol) and MeI (49.7 μL, 798 μmol) and stirred in a sealed tube at 65° C. for 1 h 30 min. The reaction mixture was cooled to rt and diluted with CH2Cl2, washed with H2O, dried (Na2SO4) and the solvent removed in vacuo to give 6-fluoro-5-methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde as an intense yellow, vitreous solid (72.3 mg), 65% pure according to LC/MS, which was directly used in the subsequent Grignard addition.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ebadf46c14f14066b6212822b37197b5
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…