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

HRID 510264Notes

Reaction equation

HRID 510264 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:37]([CH3:38])=[CH:36][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=3)[S:21][C:17]=2[C:16]=1Br)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:40][C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=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]([C:15]1[C:37]([CH3:38])=[CH:36][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=3)[S:21][C:17]=2[C:16]=1[C:44]1[CH:45]=[CH:46][C:41]([Cl:40])=[CH:42][CH:43]=1)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86699794(S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Product 1

HCID 86699795(S)-2-(2-(3-(benzyloxy)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalateYield 97.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of (S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (100 mg, 0.164 mmol), 4-chlorophenylboronic acid (38 mg, 0.246 mmol), 2N K2CO3 (400 μL), Pd(PPh3)4 (18 mg, 0.016 mmol) in dioxane in sealed tube was heated at 120° C. After the reaction is finished, the 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 (0-50% EtOAc in Hexanes) to give the product (103 mg, 97%). LCMS-ESI+: calc'd for C38H40ClNO4S: 642.2 (M+H+); Found: 642.3 (M+H+).

Workup

  1. washthe reaction mixture was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column (0-50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-1b7adee157b74e8091ce663ff8444acf
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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