Isopropyl iodide → HCID 60054823, compound

HRID 489246Notes

Reaction equation

HRID 489246 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]3([C@H:18]([C:19]4[CH:24]=[CH:23][C:22]([C:25]5[CH:26]=[N:27][CH:28]=[N:29][CH:30]=5)=[CH:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[N:11]([CH3:31])[C:10]2=[O:32])[CH:5]=[C:6]([Cl:8])[CH:7]=1.I[CH:34]([CH3:36])[CH3:35].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]3([C@H:18]([C:19]4[CH:20]=[CH:21][C:22]([C:25]5[CH:30]=[N:29][CH:28]=[N:27][CH:26]=5)=[CH:23][CH:24]=4)[CH2:17][N:16]([CH:34]([CH3:36])[CH3:35])[CH2:15]3)[N:11]([CH3:31])[C:10]2=[O:32])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 60054739HCID 60054739, compound

Product 1

HCID 60054823HCID 60054823, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 67 (49.7 mg, 0.11 mmol), 2-iodo propane (26 μl, 0.26 mmol) and K2CO3 (36 mg, 0.26 mmol) was heated at 80° C. for 25 h in acetonitrile (2 ml). After cooling to room temperature, the insoluble salts were removed and the filtrate concentrated to dryness. The residue was partitioned between DCM/water. The organic layer was concentrated in vacuo and chromatographed over silica gel (eluent: DCM/MeOH 95/5) to yield the above-titled compound as an amorphous white solid (38.1 mg). 1H NMR (CDCl3): 9.21 (1H, s), 8.92 (2H, s), 7.56 (2H, d, J=8.0 Hz), 7.33 (2H, d, J=8.0 Hz), 7.20 (1H, m), 6.61 (2H, d, J=1.5 Hz), 3.90 (1H, dd, J1=12 Hz , J2=6 Hz), 3.4-3.5 (2H, m), 3.2-3.4 (1H, m), 3.28 (3H, s), 3.09 (1H, d, J=11 Hz), 2.79 (1H, m), 1.23 (6H, m).

Workup

  1. customthe insoluble salts were removed
  2. concentrationthe filtrate concentrated to dryness
  3. customThe residue was partitioned between DCM/water
  4. concentrationThe organic layer was concentrated in vacuo
  5. customchromatographed over silica gel (eluent: DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-73815f33ac524782abbae9a6a3101070
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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