Water → HCID 57635634, compound

HRID 535963Notes

Reaction equation

HRID 535963 reaction equation
Br[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:15][C@@H:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH:19][CH3:20])=[O:18])=[O:14])[N:3]=1.[C:25]([Si:29]([CH3:45])([CH3:44])[O:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/B1OC(C)(C)C(C)(C)O1)([CH3:28])([CH3:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.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>[Si:29]([O:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:15][C@@H:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH:19][CH3:20])=[O:18])=[O:14])[N:3]=1)([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:44])[CH3:45]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16217344(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silaneHCID 57635118HCID 57635118, compound

Product 1

HCID 57635634HCID 57635634, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of compound 324 (0.10 g, 0.25 mmol) in dioxane (2 mL) was (E)-tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyloxy)silane (0.115 g, 0.50 mmol), followed by K2CO3 (0.069 g, 0.50 mmol) and water (0.40 mL). The resulting mixture was degassed with nitrogen and Pd(PPh3)4 (0.023 g, 0.02 mmol) was added. The mixture was heated in microwave reactor at 160° C. for 20 min. The mixture was diluted with EtOAc, and filtered through celite. The organic layer was concentrated, washed with water, dried over anhydrous Na2SO4 and concentrated again. The residue was purified using PL-Thiol MP SPE tube to provide compound 47A (0.126 g, 99%). LCMS (+ESI) m/z 506.4 [M+H]+.

Workup

  1. additionwas added
  2. filtrationfiltered through celite
  3. concentrationThe organic layer was concentrated
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated again
  7. customThe residue was purified

Sources & evidence

ORD record
ord-a9c132b42dc54c6f92d14221fba78630
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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