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Cesium carbonate → 1-(Tetrahydro-1,1-dioxido-3-thienyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2090414
Notes
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Reaction equation

HRID 2090414 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Br[CH:16]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[O:21]=[S:18]1(=[O:22])[CH2:19][CH2:20][CH:16]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 956373-Bromotetrahydrothiophene 1,1-dioxideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 670506351-(Tetrahydro-1,1-dioxido-3-thienyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6342Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), 3-bromotetrahydrothiophene 1,1-dioxide (56 mg, 0.28 mmole; ChemBridge, Cat. No. 4011807), cesium carbonate (0.25 g, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. overnight. After cooling it was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4. After filtration the filtrate was concentrated to yield 74 mg of the product. LCMS (M+H)+: m/z=313.1

Workup

  1. temperatureAfter cooling it
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-ba42a1a3300c4cb188ca33bdeebbfd4a
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436008B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes