Vinyl Acetate → HCID 67186185, compound

HRID 885993Notes

Reaction equation

HRID 885993 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH2:15][N:14]([C:18]4[S:19][C:20]5[C:21](=[O:29])[NH:22][C:23]([CH3:28])([CH3:27])[CH2:24][C:25]=5[N:26]=4)[C:13]=3[CH:30]=2)[CH:3]=1.C(OC=C)(=O)C.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:27][C:23]1([CH3:28])[NH:22][C:21](=[O:29])[C:20]2[S:19][C:18]([N:14]3[C:13]4[CH:30]=[C:9]([C:4]5[CH:3]=[CH:2][N:7]=[C:6]([CH3:8])[N:5]=5)[CH:10]=[CH:11][C:12]=4[O:17][CH2:16][CH2:15]3)=[N:26][C:25]=2[CH2:24]1

Participants

7

Reactant 4

HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 87302243HCID 87302243, compound

Product 1

HCID 67186185HCID 67186185, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of Example 456 (100 mg, 0.227 mmol) in DMF (4 mL) was added vinyl acetate (0.11 mL, 1.13 mmol), triethylamine (0.06 mL, 0.454 mmol), 1,3-bis-(diphenylphosphino)propane (10 mg, 0.023 mmol) and palladium acetate (2.5 mg, 0.011 mmol). The mixture was heated to 140° C. under microwave irradiation for 1 h. The resulting suspension was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to yield the title compound (34 mg, 35%) as an off-white solid. δH (CDCl3) 8.72 (1H, d, J 2.1 Hz), 8.65 (1H, d, J 5.4 Hz), 7.84 (1H, dd, J 8.6 and 2.1 Hz), 7.44 (1H, d, J 5.4 Hz), 7.07 (1H, d, J 8.6 Hz), 5.24 (1H, br. s), 4.47-4.28 (2H, m), 4.30-4.11 (2H, m), 2.90 (2H, s), 2.78 (3H, s), 1.41 (6H, s). LCMS (ES+) 408.0 (M+H)+, RT 2.83 minutes (Method 1).

Workup

  1. customThe resulting suspension was partitioned between DCM (50 mL) and water (50 mL)
  2. washthe organic fraction was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-addc7c961d06477f895e6a5bb0e20977
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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