Sodium Acetate → HCID 67440378, compound

HRID 2096287Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:7]([N:9]([CH2:21][C:22]#[C:23][C:24]2[CH:41]=[CH:40][C:27]([CH2:28][NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:26][CH:25]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])=[O:8])[NH:5][CH:6]=1.C([O-])(=O)C.[Na+]>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[O:8])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])[CH:21]=[C:22]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:40][CH:41]=3)[N:5]2[CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of EXAMPLE 37B (21.0 g, 34 mmol) in N,N-dimethylformamide (900 ml) was added sodium acetate (2.81 g, 34 mmol), tetrabutyl ammonium chloride (9.51 g, 34 mmol) and palladium(II) acetate (767 mg, 3.4 mmol). The mixture was heated at 120° C. for 30 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with water, and concentrated. The residue was purified by flash chromatography (50% ethyl acetate in hexane) to afford the title compound. LC-MS (ESI): m/z 616, 618 (M, M+2), RT: 2.38 minutes.

Workup

temperatureAfter cooling
customthe reaction mixture was partitioned between ethyl acetate and brine
washThe organic phase was washed with water
concentrationconcentrated
customThe residue was purified by flash chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-83634dca423145bcae0fe9a1c5305904
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450320B2

Reaction notes

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