Cesium carbonate → HCID 58034428, compound

HRID 1914840Notes

Reaction equation

HRID 1914840 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:29]=[C:28]4[C:23]([CH:24]=[N:25][C:26]5[N:27]4[N:30]=[C:31]([CH3:33])[CH:32]=5)=[C:22](Cl)[C:21]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:16][CH:15]=2)[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:42]B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>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(Cl)Cl.O1CCOCC1>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:29]=[C:28]4[C:23]([CH:24]=[N:25][C:26]5[N:27]4[N:30]=[C:31]([CH3:33])[CH:32]=5)=[C:22]([CH3:42])[C:21]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:16][CH:15]=2)[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 139377Methylboronic AcidHCID 58034362HCID 58034362, compound

Product 1

HCID 58034428HCID 58034428, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 20 ml scintillation vial containing Compound (20-4) (40 mg, 0.07 mmol, 1 eq.), methylboronic acid (84 mg, 1.4 mmol, 2 eq.), Cs2CO3 (226 mg, 0.70 mmol, 1 eq.), and dioxane (5.0 ml) was evacuated and flushed three times with nitrogen. Then PdCl2(dppf)-CH2Cl2 (24 mg, 0.03 mmol, 0.5 eq.) was added and the resulting solution was evacuated and flushed three times with nitrogen. The mixture was heated at 80° C. for 2.5 h. Then it was allowed to cool. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (10 mL). After filtration and concentration, it was purified by silica gel chromatography by using MeOH and CH2Cl2 as the mobile phases to furnish Compound (20-5) as a yellowish solid.

Workup

  1. customwas evacuated
  2. customflushed three times with nitrogen
  3. customthe resulting solution was evacuated
  4. customflushed three times with nitrogen
  5. temperatureto cool
  6. customThe solvent was removed in vacuo
  7. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  8. filtrationAfter filtration and concentration, it
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-d26ccfb217d34c91ba1f32637847bc9f
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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