Methyl iodide → HCID 10108758, compound

HRID 915503Notes

Reaction equation

HRID 915503 reaction equation
C[O:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=O.C(OC(C1C2C=C(OC)C=CC=2OC=1C1C=CC(F)=CC=1)=O)C.CI.C(=O)([O-])[O-].[K+].[K+].[C:54](#[N:56])C>>[CH3:54][NH:56][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:2]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 68679956HCID 68679956, compoundHCID 68682182HCID 68682182, compound

Product 1

HCID 10108758HCID 10108758, compoundYield 78%

Procedure

Preparation of compound 12(b)(i) and compound 12(b)(ii) (2-(4-fluoro-phenyl)-5-methoxy-benzofuran-3-carboxylic acid methyl ester and 2-(4-fluoro-phenyl)-5-methoxy-benzofuran-3-carboxylic acid ethyl ester). Methyl iodide (0.43 mL, 6.99 mmol) was added to a mixture of the compounds 12(a)(i) and 12(a)(ii) (1.00 g, 3.49 mmol), potassium carbonate (milled, 1.21 g, 8.73 mmol) and anhydrous acetonitrile (15 mL) under an argon atmosphere. The reaction mixture was heated to reflux under argon for 18 hours, and then cooled to room temperature and stirred for 24 hours. The mixture was diluted with acetonitrile (10 mL) and filtered, followed by evaporation of the solvent. The crude solid was diluted with 60:40 ethyl acetate/hexanes, re-filtered, and purified by HPLC (silica gel, ethyl acetate/hexanes) to provide 0.85 g (78%) of the desired product.

Workup

  1. customPreparation of compound 12(b)(i)
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux under argon for 18 hours
  4. filtrationfiltered
  5. customfollowed by evaporation of the solvent
  6. additionThe crude solid was diluted with 60:40 ethyl acetate/hexanes
  7. filtrationre-filtered
  8. custompurified by HPLC (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-04045e7daeac4fa2ba9d02b13088bfcb
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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