Potassium Carbonate → HCID 66863626, compound

HRID 1186684Notes

Reaction equation

HRID 1186684 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27339602-Thiopheneboronic acidHCID 2776849Methyl 2-bromo-5-methoxybenzoate

Product 1

HCID 66863626HCID 66863626, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a degassed solution of methyl 2-bromo-5-methoxybenzoate 8 (0.25 g, 1.020 mmol), 2-thiophene boronic acid 9 (0.170 g, 1.326 mmol), tri-o-tolylphosphine (0.093 g, 0.306 mmol), and K2CO3 (0.423 g, 3.06 mmol) in DME (3 mL) and water (1 mL) was added Pd(Ph3P)4 (0.077 g, 0.066 mmol) and the reaction mixture was placed in a preheated oil bath at 85° C. and stirred overnight. The next morning the reaction was complete by HPLC therefore it was solvent evaporated, diluted with DCM, washed with water, brine, dried over MgSO4, filtered and solvent evaporated to provide compound 10 (0.13 g, 52% yield) as a colorless oil after purification by Biotage (0 to 10% EtOAc in Hexane). LRMS (ESI): (calc.) 248.05 (found) 249.1 (MH)+

Workup

  1. customthe reaction mixture was placed in a preheated oil bath at 85° C.
  2. customevaporated
  3. additiondiluted with DCM
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-eb793c43ba4148e885824c6418b15317
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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