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

HRID 879278Notes

Reaction equation

HRID 879278 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20](Cl)[S:21][C:17]=2[C:16]=1[Br:26])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:27]([O:34][C:35]1[CH:36]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:39][CH:40]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:36]=3)[S:21][C:17]=2[C:16]=1[Br:26])[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 162174672-[3-(Benzyloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70981474(S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Product 1

HCID 86699794(S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalateYield 58.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (130 mg, 0.282 mmol) in dioxane, was added 3-benzyloxyphenylboronic acid pinacol ester (105 mg, 0.338 mmol), Pd(PPh3)4 (16 mg, 0.014 mmol), 2N K2CO3 (700 μL). The reaction mixture in sealed tube was heated at 95° C. for 1.5hs. Then the reaction was cooled down. The reaction mixture was washed by sat. NaHCO3, and extracted by EtOAc. The organic phase was filtered, concentrated down, purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product (100 mg, 58%). LCMS-ESI+: calc'd for C32H36BrNO4S: 610.2 (M+H+); Found: 610.2 (M+H+).

Workup

  1. temperatureThen the reaction was cooled down
  2. washThe reaction mixture was washed by sat. NaHCO3
  3. extractionextracted by EtOAc
  4. filtrationThe organic phase was filtered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-9459824473314263a7a13c8da5b23e92
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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