Cesium carbonate → HCID 53387574, compound

HRID 2077615Notes

Reaction equation

HRID 2077615 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[C:23]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][N:19]=1>C1COCC1.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]>[O:8]1[C:4]2[CH:3]=[C:2]([C:21]3[CH:22]=[C:23]([NH:24][S:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:18]([Cl:17])=[N:19][CH:20]=3)[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 179028006-Bromo-1,3-benzoxazoleHCID 53363355n-[2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-4-fluorobenzene-1-sulfonamide

Product 1

HCID 53387574HCID 53387574, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a microwave vial equipped with a stirbar and charged with 6-bromobenzo[d]oxazole (0.050 g, 0.25 mmol), cesium carbonate (0.25 g, 0.76 mmol), PdCl2(dppf)*DCM (0.037 g, 0.045 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.10 g, 0.25 mmol) in THF (3 ml) was added water (0.5 ml). The vial was capped and placed into CEM Microwave for 10 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired material in the mixture. The mixture was diluted with water and the organic layer was extracted with DCM and brine solution. The organics were collected, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was recrystallized from 5:1 DCM/MeOH and Hexanes to give N-(5-(benzo[d]oxazol-6-yl)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.040 g, 39% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 404 (MH+).

Workup

  1. customTo a microwave vial equipped with a stirbar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)
  4. extractionthe organic layer was extracted with DCM and brine solution
  5. customThe organics were collected
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude was recrystallized from 5:1 DCM/MeOH and Hexanes

Sources & evidence

ORD record
ord-79e4153daefa4bae86622215cac436e9
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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