Sodium Iodide → HCID 68288888, compound

HRID 541465Notes

Reaction equation

HRID 541465 reaction equation
C[O:2][CH:3]1[CH2:35][C:7]2[NH:8][C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)=[O:17])=[N:10][C:6]=2[CH2:5][CH2:4]1.C(#N)C.Cl[Si](Cl)(Cl)Cl.[I-].[Na+]>ClCCl>[OH:2][CH:3]1[CH2:35][C:7]2[NH:8][C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=4)[CH2:22][CH2:23]3)=[O:17])=[N:10][C:6]=2[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 24816Silicon tetrachlorideHCID 68288681HCID 68288681, compound2×

Product 1

HCID 68288888HCID 68288888, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Into around-bottom flask, was placed a solution of 4-(1-(5-(6-methoxy-4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (compound 459, 80 mg, 0.17 mmol, 1.0 equiv) in a solvent mixture of acetonitrile and dichloromethane (10/10 mL). Tetrachlorosilane (32 mg, 0.19 mmol, 1.1 equiv) and sodium iodide (28 mg, 0.19 mmol, 1.1 equiv) were added to the reaction and the resulting mixture was stirred overnight at 20° C. The reaction was quenched with aqueous sodium bicarbonate (10 mL) and the aqueous was extracted with ethyl acetate (3×10 mL). The combined organics was dried (Na2SO4), filtered and concentrated in vacuo and the residue was purified by silica gel chromatography with ethyl acetate as the eluent to obtain the title compound as a yellow solid (7.1 mg, 9%). m/z (ES+) 455 (M+H)+.

Workup

  1. customInto around-bottom flask, was placed
  2. customThe reaction was quenched with aqueous sodium bicarbonate (10 mL)
  3. extractionthe aqueous was extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organics was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-de22d54fc9424e06b180931421dd6b41
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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