Potassium Carbonate → HCID 68782591, compound

HRID 1441301Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][NH:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:26]([O:33][CH2:34][N:35]1[C:43]2[C:38](=[CH:39][C:40](B(O)O)=[CH:41][CH:42]=2)[C:37]([CH3:47])=[N:36]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.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.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][NH:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]([C:40]2[CH:39]=[C:38]3[C:43](=[CH:42][CH:41]=2)[N:35]([CH2:34][O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:36]=[C:37]3[CH3:47])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of the compound from step C (0.42 g, 1.17 mmol), the boronic acid 5 from step B (0.47 g, 0.58 mmol), and potassium carbonate (0.16 g, 1.17 mmol) in DMF/water (5 mL/2 mL) was degassed, placed under nitrogen and was added to PdCl2(dppf) (29 mg, 0.035 mmol). The mixture was heated at 75° C. for 11 h under nitrogen, and then cooled and extracted with ethyl acetate (50 mL×2). Chromatography on silica eluting with a 20% to 70% gradient of ethyl acetate/hexane gave the title compound (0.54 g, 81%). LCMS (+APCI) m/z 579 (M+H).

Workup

temperaturecooled
extractionextracted with ethyl acetate (50 mL×2)

Sources & evidence

ORD record: ord-bde0c1c689144123bd830f430cf561ce
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655662B2

Reaction notes

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