4-Carboxyphenylboronic Acid → HCID 59822344, compound

HRID 1678509Notes

Reaction equation

HRID 1678509 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:26]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)([OH:28])=[O:27]>C(=O)(O)[O-].[Na+].COCCOC>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([S:10](=[O:12])(=[O:11])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[CH:3][C:2]=1[C:32]1[CH:33]=[CH:34][C:29]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 4879792HCID 4879792, compound

Product 1

HCID 59822344HCID 59822344, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-bromo-4-methoxy-N-(4-morpholin-4-yl-phenyl)-benzenesulfonamide (460 mg) and 4-carboxy-phenyl boronic acid (196 mg) in saturated sodium bicarbonate solution (4 ml) and DME (8 ml) was heated to reflux in the presence of tetrakis(triphenylphosphine)palladium0 for 16 h. The mixture was allowed to cool and was evaporated. The residue was then suspended in water and 2M HCl added until the effervescence ceased. The resulting light grey solid was collected and dried (490 mg)

Workup

  1. temperaturewas heated
  2. temperatureto cool
  3. customwas evaporated
  4. addition2M HCl added until the effervescence
  5. customThe resulting light grey solid was collected
  6. customdried (490 mg)

Sources & evidence

ORD record
ord-2ab3e36972fe4f809ed021fa6ae6ff73
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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