Water → HCID 21906677, compound

HRID 1247588Notes

Reaction equation

HRID 1247588 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[CH:19]=[C:18](I)[CH:17]=[N:16][C:15]=3[Cl:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([OH:26])[CH:24]=[CH2:25].C(=O)(O)[O-].[Na+].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[CH:19]=[C:18]([CH2:25][CH2:24][CH:23]=[O:26])[CH:17]=[N:16][C:15]=3[Cl:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 21906711HCID 21906711, compound

Product 1

HCID 21906677HCID 21906677, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(1-adamantylmethyl)-5-iodo-2-chloronicotinamide (Example 3(i)) (2.15 g), allyl alcohol (0.58 g), palladium (II) acetate (0.015 g), sodium bicarbonate (1.05 g) and tetra-butyl ammonium chloride (1.39 g) were stirred together in anhydrous N,N-dimethylformamide (20 ml) for 20 hours. The reaction mixture was poured into water (100 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:iso-hexane (1:1) to afford the sub-titled compound (0.65 g).

Workup

  1. extractionextracted into ethyl acetate (3×25 ml)
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:iso-hexane (1:1)

Sources & evidence

ORD record
ord-cbbb5374e8ec4ff385e1032a33f9a7a9
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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