Sodium Carbonate → HCID 22988269, compound

HRID 987163Notes

Reaction equation

HRID 987163 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(CCO)C=CC=CC=1.O>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:18]([OH:20])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 22106702HCID 22106702, compound

Product 1

HCID 22988269HCID 22988269, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 70030519HCID 70030519, compoundSolvent

Conditions

Temperature
100 °C

Procedure

To a sealed tube containing 2-[5-bromo-1-benzyl-1H-indole-2carboxylic acid (100 mg, 0.303 mmol) and 2-thiopheneboronic acid (116 mg, 0.909 mmol), (C6H5)4Pd (42 mg, 0.036 mmol), Na2CO3 (2,42 mmol) in a mixture of benzene-ethanol-H2O (5/1/2=v/v, 4.5 mL) was heated at 100° C. for 23 h. The mixture was poured onto diethyl ether and adjusted to pH 3 before extracting with diethyl ether. The organic layer was washed with NaH2PO4, dried over MgSO4 and evaporated to give the crude product which was purified on silica gel column (15% EtOAc in hexane with 1% HCOOH) to give 65 mg of the product.

Workup

  1. additionThe mixture was poured onto diethyl ether
  2. extractionbefore extracting with diethyl ether
  3. washThe organic layer was washed with NaH2PO4
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give the crude product which
  7. customwas purified on silica gel column (15% EtOAc in hexane with 1% HCOOH)

Sources & evidence

ORD record
ord-4833192a112e43468732801ea592bf13
Source dataset
uspto-grants-2003_10
Patent number
US06630496B1

Reaction notes

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