Benzophenone imine → HCID 66801618, compound

HRID 2366304Notes

Reaction equation

HRID 2366304 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C1(C(C2C=CC=CC=2)=[NH:26])C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH2:26])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 862804124-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine

Product 1

HCID 66801618HCID 66801618, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (1.00 g, 2.80 mmol), diphenylmethanimine (607 mg., 3.40 mmol), Pd2(dba)3 (128 mg, 0.140 mmol), BINAP (174 mg, 0.280 mmol), sodium tert-butoxide (403 mg, 4.20 mmol), and toluene (15.0 mL). The mixture was degassed with nitrogen for 10 min. The resulting mixture was irradiated in a microwave reactor at 130° C. for 1 hour and then cooled to room temperature. The mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:10 to 1:2) to give the desired product as a solid (320 mg, 38.7% yield). LCMS (ESI) m/z: 296 [M+H+].

Workup

  1. customThe mixture was degassed with nitrogen for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 130° C. for 1 hour
  3. filtrationThe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with ethyl acetate/petroleum ether (1:10 to 1:2)

Sources & evidence

ORD record
ord-aff6222aaaf24af4b658131729accfba
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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