Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(5-methoxypyridin-3-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol

HRID 879280Notes

Reaction equation

HRID 879280 reaction equation
C([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)(=O)C(C)(C)C.[CH3:46][O:47][C:48]1[CH:49]=[N:50][CH:51]=[C:52](B2OC(C)(C)C(C)(C)O2)[CH:53]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>O1CCOCC1.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.CO>[C:42]([O:41][C@@H:9]([C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:52]4[CH:51]=[N:50][CH:49]=[C:48]([O:47][CH3:46])[CH:53]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[CH2:8][OH:7])([CH3:43])([CH3:44])[CH3:45]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86699797(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate

Product 1

HCID 86699796(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(5-methoxypyridin-3-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethanolYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

The reaction mixture of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy) phenyl)benzo[d]thiazol-6-yl)ethyl pivalate (20 mg, 0.029 mmol), 3-methoxypyridine-5-boronic acid pinacol ester (10 mg, 0.043 mmol), 2N K2CO3 (70 μL), Pd(PPh3)4 (3.3 mg, 0.0029 mmol) in dioxane (1 mL) was heated at 120° C. in sealed tube for 2 hours. After the reaction finished, the reaction was cooled down, to the reaction mixture was added MeOH (1 mL), 2N NaOH (500 μL) and heated at 45° C. for 3 hours. Then reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product (10 mg, 62%). LCMS-ESI+: calc'd for C32H31ClN2O3S: 559.2 (M+H+); Found: 559.2 (M+H+).

Workup

  1. temperaturethe reaction was cooled down, to the reaction mixture
  2. temperatureheated at 45° C. for 3 hours
  3. customThen reaction mixture
  4. washwas washed by sat. NaHCO3
  5. extractionextracted by EtOAc
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. custompurified by silica gel column
  10. washeluting by 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-51759c0b0a0f43189e3204a261f07c8c
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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