Potassium → HCID 68805556, compound

HRID 1373197Notes

Reaction equation

HRID 1373197 reaction equation
C[O:2][C:3]([C:5]1([F:24])[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[CH:13][C:8]2=[N:9][CH2:10][N:11]([CH3:12])[C:7]2=[CH:6]1)=[O:4].[K].C(Cl)Cl.CO>O1CCCC1>[F:24][C:5]1([C:3]([OH:4])=[O:2])[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[CH:13][C:8]2=[N:9][CH2:10][N:11]([CH3:12])[C:7]2=[CH:6]1

Participants

5

Reactant 3

HCID 5462222PotassiumHCID 21226129Dichloromethane methanolHCID 68804660HCID 68804660, compound

Product 1

HCID 68805556HCID 68805556, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoro-6-(2-fluoro-4-iodo-phenylamino)-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (136.3 g, 0.305 mol) in tetrahydrofuran (1.5 L) was added potassium trimethylsilonate (155.95 g, 1.23 mol) at room temperature (after completion of the addition the reaction mixture became dark brown solution). The reaction mixture was stirred for 3.5 h (completion of reaction is confirmed by TLC-DCM:MeOH 1:9), quenched with water (25 ml) and evaporated under vacuum to remove THF. The residue was then adjusted to pH 1 with conc. HCl and the solid (creamy white) was filtered, washed with water (2×200 ml) then dried to give title compound. Yield: 96 g (52.53%).

Workup

  1. additionafter completion of the addition the reaction mixture
  2. customquenched with water (25 ml)
  3. customevaporated under vacuum
  4. customto remove THF
  5. filtrationthe solid (creamy white) was filtered
  6. washwashed with water (2×200 ml)
  7. customthen dried

Sources & evidence

ORD record
ord-356a43a108cd43409e238b0389642594
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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