Potassium Iodide → HCID 68844703, compound

HRID 238893Notes

Reaction equation

HRID 238893 reaction equation
[C:1]([O:5][C:6](=[O:23])[C:7]([NH:10][C:11]([C:13]1[CH:21]=[CH:20][C:16]2[S:17][CH:18]=[CH:19][C:15]=2[C:14]=1[OH:22])=[O:12])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1.[I-].[K+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:9])([NH:10][C:11]([C:13]1[CH:21]=[CH:20][C:16]2[S:17][CH:18]=[CH:19][C:15]=2[C:14]=1[O:22][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:37]=1)=[O:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 688411722-[(4-Hydroxy-benzo[b]thiophene-5-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 68844703HCID 68844703, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

80 mg 2-[(4-Hydroxy-benzo[b]thiophene-5-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester, 90 mg cesium carbonate, 55 mg of 1-bromomethyl-4-trifluoromethyl-benzene and 8 mg potassium iodide were dissolved in 1 ml of N,N-dimethylformamide and stirred for 1 h at 60° C. 10 ml of ethyl acetate and 10 ml of brine were added to the reaction. The organic layer was separated and washed again with 10 ml of brine. It was then dried over sodium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate) to afford 113 mg of 2-methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester

Workup

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of brine
  3. dry with materialIt was then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-264db762ea9c48dea0421d77d60cb5b6
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

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