Potassium Carbonate → HCID 90290199, compound

HRID 2170385Notes

Reaction equation

HRID 2170385 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:27]2[CH:28]=[CH:29][C:30]([Cl:42])=[C:31]3[C:35]=2[N:34]([CH3:36])[N:33]=[C:32]3[NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:5]([C@@H:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:6][C:7]=1Br.[C:43]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.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]>[NH2:1][C:2]1[CH:3]=[C:4]([C:27]2[CH:28]=[CH:29][C:30]([Cl:42])=[C:31]3[C:35]=2[N:34]([CH3:36])[N:33]=[C:32]3[NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:5]([C@@H:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:6][C:7]=1[CH3:43]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 90290198HCID 90290198, compound

Product 1

HCID 90290199HCID 90290199, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a flask of 47A (255 mg, 0.37 mmol) in dioxane, K2CO3 (179 mg, 1.30 mmol), PdCl2(dppf) (27 mg, 0.037 mmol) and trimethyl boroxine (0.052 mL, 0.37 mmol) was added to the mixture. The reaction mixture was heated at 100° C. for 3 h. The reaction was cooled down and the solution partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined extracts dried, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to provide the title compound. MS (m/z) 621 [M+H]+.

Workup

  1. temperatureThe reaction was cooled down
  2. customthe solution partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. customthe combined extracts dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-12cf5e2e30d046d2afd9a9a0b7c2c45f
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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