Potassium Acetate → HCID 178457730, compound

HRID 2059724Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([NH:17][C:18]([CH3:26])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[O:16])=[CH:10][N:9]=2)[CH:3]=1.[C:27]([O-:30])(=[O:29])C.[K+]>CS(C)=O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[OH:14][C:12]1[C:11]([C:15]([NH:17][C:18]([CH3:26])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])=[O:16])=[CH:10][N:9]=[C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=2)[C:27]([OH:30])=[O:29])[N:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To the product of Example 1 (0.198 g, 0.479 mmol) in DMSO (5.0 mL) was added potassium acetate (0.188 g, 1.916 mmol), palladium(II) acetate (5.38 mg, 0.024 mmol), and dppf (0.053 g, 0.096 mmol). The reaction was stirred under a CO atmosphere and heated at 120° C. for 30 min. The reaction was diluted with EtOAc, washed with aq. HCl (1M) and concentrated. The residue was purified by preparative HPLC (Non-Polar Method). The material was further purified by flash chromatography on silica gel eluted with EtOH to afford the title compound. HPLC/MS: 379.0 (M+1); Rt=2.62 min.

Workup

washwashed with aq. HCl (1M)
concentrationconcentrated
customThe residue was purified by preparative HPLC (Non-Polar Method)
customThe material was further purified by flash chromatography on silica gel
washeluted with EtOH

Sources & evidence

ORD record: ord-1378448ed2574cacbf18aa61ad2d0205
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278304B2

Reaction notes

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