Sodium Iodide → HCID 178522749, compound

HRID 1247611Notes

Reaction equation

HRID 1247611 reaction equation
[I-].[Na+].C[Si](Cl)(C)C.[C:8]12([CH2:18][NH:19][C:20](=[O:30])[C:21]3[C:26]([Br:27])=[CH:25][N:24]=[C:23]([O:28]C)[CH:22]=3)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>C(#N)C.O>[C:8]12([CH2:18][NH:19][C:20](=[O:30])[C:21]3[C:26]([Br:27])=[CH:25][N:24]=[C:23]([OH:28])[CH:22]=3)[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:16]3)[CH2:15]1)[CH2:17]2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 21906706N-(1-Adamantylmethyl)-5-bromo-2-methoxyisonicotinamide

Product 1

HCID 178522749HCID 178522749, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Sodium iodide (0.48 g) was added to a solution of trimethylsilylchloride (0.41 ml) in acetonitrile (30 ml) and the mixture was stirred for 1 hour. N-(1-Adamantylmethyl)-5-bromo-2-methoxyisonicotinamide (0.94 g) (Example 35(i)) was then added and the reaction mixture was heated at 60° C. under nitrogen for 3 hours. The reaction mixture was diluted with water (150 ml) and the resultant solid was collected by filtration and dried by means of ethanol/toluene azeotrope. The solid was triturated with diethyl ether and collected by filtration to afford the sub-titled compound (0.70 g).

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. dry with materialdried by means of ethanol/toluene azeotrope
  3. customThe solid was triturated with diethyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a159eec3ad7940d09e27f88107eef88b
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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