Water → HCID 58495669, compound

HRID 1191108Notes

Reaction equation

HRID 1191108 reaction equation
Br[C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:6]=1.C([O-])([O-])=O.[Na+].[Na+].[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[S:3][C:4]([C:7](=[O:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:6]=2)=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 58495549HCID 58495549, compound

Product 1

HCID 58495669HCID 58495669, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-bromo-5-(3,3-dimethylbutyryl)-thiophene (187 mg, 0.7 mmol) in dioxane (7 mL) add a solution of aqueous 2M Na2CO3 (0.9 mL), [4-(N-tert-butoxycarbonyl-aminomethyl)phenyl]boronic acid (216 mg, 0.8 mmol) and tetrakis(triphenylphosphine)-palladium(0) (41 mg, 0.03 mmol). Heat the mixture at 90° C. overnight. Cool at room temperature, add water and extract with EtOAc. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate (174 mg, 63%).

Workup

  1. temperatureCool at room temperature
  2. extractionextract with EtOAc
  3. dry with materialDry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-07b9f9e2d4af44a7b6340308d0f226fb
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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