Potassium Phosphate, Tribasic → HCID 86700162, compound

HRID 879358Notes

Reaction equation

HRID 879358 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](Cl)[CH:20]=3)[S:18][C:14]=2[C:13]=1[O:29][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:37][N:38]1[C:42]2[CH:43]=[CH:44][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:46][C:41]=2[N:40]([CH3:56])[C:39]1=[O:57].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.CCOC(C)=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]>[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:45]4[CH:44]=[CH:43][C:42]5[N:38]([CH3:37])[C:39](=[O:57])[N:40]([CH3:56])[C:41]=5[CH:46]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[O:29][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 86700163HCID 86700163, compoundHCID 867001641362243-58-0

Product 1

HCID 86700162HCID 86700162, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(2-(2-chloropyridin-4-yl)-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate (26.0 mg, 0.046 mmol), 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (20.0 mg, 0.069 mmol) and K3PO4 (29.2 mg, 0.138 mmol) in dioxane (1.0 mL) and H2O (0.1 mL) was degassed for 5 min, treated with PdCl2(dppf) (5.0 mg, 0.007 mmol). The resulting mixture was heated at 100° C. for 8 min. The reaction mixture was diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C31H32F3N4O7S2: 693.2; found: 693.1.

Workup

  1. extractionextracted with H2O, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4526aaece86b44dcb620b515be5fccc3
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…