Cesium carbonate → HCID 117678052, compound

HRID 1507492Notes

Reaction equation

HRID 1507492 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.I[C:12]1[C:13]([NH:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]2)=[N:14][C:15]([S:20][CH3:21])=[N:16][C:17]=1[O:18][CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:12]3[C:13]([NH:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]4)=[N:14][C:15]([S:20][CH3:21])=[N:16][C:17]=3[O:18][CH3:19])=[N:7][C:6]=2[CH:10]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 187861675-Fluoro-1,3-benzothiazoleHCID 117677347HCID 117677347, compound

Product 1

HCID 117678052HCID 117678052, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

DMF (4.3 mL) was added to a 125 mL round-bottom flask containing 5-fluorobenzo[d]thiazole (268 mg, 1.749 mmol). Compound 23 (420 mg, 0.874 mmol), Pd(Ph3P)4 (202 mg, 0.175 mmol), Cs2CO3 (1709 mg, 5.25 mmol) and CuI (33.3 mg, 0.175 mmol) were then added. The mixture was degassed placed in an oil bath that was preheated to 100° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with water and ethyl acetate and filtered through celite. The organics were then separated and the water layer was washed with ethyl acetate. The organics were combined, washed with brine (×3), dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the title compound as a white solid. 1H NMR (CDCl3) δ 10.81-10.78 (m, 1H), 7.79-7.75 (m, 1H), 7.62-7.59 (m, 1H), 7.11-7.07 (m, 1H), 4.41-4.89 (m, 1H), 4.16-4.14 (m, 2H), 3.69-3.44 (m, 2H), 2.00-1.25 (m, 13H), LCMS 3.30 min, 506 (M+H)

Workup

  1. customThe mixture was degassed
  2. customplaced in an oil bath
  3. additiondiluted with water and ethyl acetate
  4. filtrationfiltered through celite
  5. customThe organics were then separated
  6. washthe water layer was washed with ethyl acetate
  7. washwashed with brine (×3)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography on silica gel
  12. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-925e6b14a4d347b997627ffb634d95f2
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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