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

HRID 879288Notes

Reaction equation

HRID 879288 reaction equation
[C:1]([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:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:46][C:47]1[CH:52]=[C:51](B(O)O)[CH:50]=[CH:49][N:48]=1.C([O-])([O-])=O.[K+].[K+]>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>[C:1]([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])[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:51]4[CH:50]=[CH:49][N:48]=[C:47]([Cl:46])[CH:52]=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)(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 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 86699806(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(2-chloropyridin-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 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 (30 mg, 0.0438 mmol), 2-chloropyridine-4-boronic acid (10 mg, 0.0657 mmol), 2N K2CO3 (100 μL), Pd(PPh3)4 (5.0 mg, 0.0044 mmol) in dioxane (2 mL) was heated at 120° C. in sealed tube for 2hs. The reaction was washed by sat. NaHCO3, extracted by EtOAc, dried by MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C36H36Cl2N2O3S: 647.2 (M+H+); Found: 647.3 (M+H+).

Workup

  1. washThe reaction was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialdried by MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-100% EtOAc in hexanes
  8. customto give the product

Sources & evidence

ORD record
ord-3ae3e88a792b4fe89b1a5cd917d75b5e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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