Potassium Carbonate → HCID 86700165, compound

HRID 879359Notes

Reaction equation

HRID 879359 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[CH:37][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:36]=[CH:35][C:28]5[N:29]([CH3:34])[C:30](=[O:33])[N:31]([CH3:32])[C:27]=5[CH:26]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:48][C:49]1[CH:54]=[CH:53][C:52](B(O)O)=[CH:51][CH:50]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[CH:37][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:36]=[CH:35][C:28]5[N:29]([CH3:34])[C:30](=[O:33])[N:31]([CH3:32])[C:27]=5[CH:26]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:52]1[CH:53]=[CH:54][C:49]([Cl:48])=[CH:50][CH:51]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86700162HCID 86700162, compound

Product 1

HCID 86700165HCID 86700165, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(2-(2-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)pyridin-4-yl)-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate (15.3 mg, 0.022 mmol), 4-chlorophenylboronic acid (4.0 mg, 0.026 mmol) and K2CO3 (9.0 mg, 0.066 mmol) in DME (0.5 mL) was added Pd(PPh3)4 (2.0 mg, 1.73×10−3 mmol). The reaction was degassed for 5 minutes with N2 and then heated at 120° C. for 6 h. After cooling, 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 C36H36ClN4O4S: 655.2; found: 655.3.

Workup

  1. customThe reaction was degassed for 5 minutes with N2
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with EtOAc
  4. extractionextracted with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a9b3396fe86048758fa6fb46f021cfd9
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…