Sodium Iodide → Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-5-yl)carbamate

HRID 2283476Notes

Reaction equation

HRID 2283476 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([O:36]C)=[C:23]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:24]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:6][C:5]=1[CH3:38])([CH3:3])[CH3:2].C[Si](Cl)(C)C.[I-].[Na+]>CC#N>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[C:23]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:22](=[O:36])[NH:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:6][C:5]=1[CH3:38])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 118261435Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-methoxy-[3,4'-bipyridin]-5-yl)carbamate

Product 1

HCID 118261436Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-5-yl)carbamateYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl (2′-((4-isopropyl-3-methylphenyl)carbamoyl)-6-methoxy-[3,4′-bipyridin]-5-yl)carbamate (216 mg, 0.42 mmol) in MeCN (50 mL) was added trimethylsilylchloride (0.18 mL, 2.1 mmol), sodium iodide (317 mg, 2.10 mmol), and the mixture was stirred at RT for 1.5 h. The precipitate was then collected by filtration. This solid was dissolved in a mixture of MeCN (1 mL) and water (50 mL) and then added to a solution of saturated aq. NaHCO3 (10 mL). The suspension was then stirred for 30 min, filtered and dried to afford benzyl (2′-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4′-bipyridin]-5-yl)carbamate (210 mg, 99% yield) as a yellow solid: MS (ES) m/z 497 (M+H).

Workup

  1. filtrationThe precipitate was then collected by filtration
  2. dissolutionThis solid was dissolved in a mixture of MeCN (1 mL) and water (50 mL)
  3. additionadded to a solution of saturated aq. NaHCO3 (10 mL)
  4. stirringThe suspension was then stirred for 30 min
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a5210e56c0ce49cf8f18de689d3abe8d
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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