Sodium Iodide → HCID 86670967, compound

HRID 515336Notes

Reaction equation

HRID 515336 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:7][CH:8]=1.[CH:19]1([CH2:22][NH:23][C:24](=[O:42])[NH:25][C:26]2[CH:41]=[CH:40][C:29]([C:30]([N:32]([CH3:39])[CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[O:31])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:19]1([CH2:22][NH:23][C:24](=[O:42])[NH:25][C:26]2[CH:41]=[CH:40][C:29]([C:30]([N:32]([CH:33]3[CH2:34][CH2:35][N:36]([CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:4]=4)[CH2:37][CH2:38]3)[CH3:39])=[O:31])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 67193617HCID 67193617, compoundHCID 86670966HCID 86670966, compound

Product 1

HCID 86670967HCID 86670967, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(3-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (84 mg, 0.249 mmol) was added to a solution of 4-(3-(cyclopropylmethyl)ureido)-N-methyl-N-(piperidin-4-yl)benzamide (82 mg, 0.249 mmol), sodium iodide (15 mg, 0.100 mmol), and potassium carbonate (103 mg, 0.748 mmol) in acetonitrile (3 mL) and the solution was stirred at ambient temperature overnight. The reaction mixture was concentrated under vacuum, dissolved in dichloromethane, washed with water, and purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 3.5% methanol/96.5% dichloromethane) to afford the title compound (57 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in dichloromethane
  3. washwashed with water
  4. custompurified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 3.5% methanol/96.5% dichloromethane)

Sources & evidence

ORD record
ord-908224f0a231490e8bd1a7e44c38cf1e
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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