Sodium Carbonate → HCID 22465129, compound

HRID 1935668Notes

Reaction equation

HRID 1935668 reaction equation
Br[C:2]1[CH:34]=[CH:33][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([CH3:25])[CH3:24])[C:10]=3[OH:32])[N:8]=[C:4]2[CH:3]=1.[S:35]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].O.C(O)CC>[S:35]1[CH:39]=[CH:38][C:37]([C:2]2[CH:34]=[CH:33][C:5]3=[N:6][N:7]([C:9]4[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:23]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)([CH3:24])[CH3:25])[C:10]=4[OH:32])[N:8]=[C:4]3[CH:3]=2)=[CH:36]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 581760Thiophene-3-boronic acidHCID 11306934HCID 11306934, compound

Product 1

HCID 22465129HCID 22465129, compoundYield 78.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

The procedure of Example 1 is followed using 5-bromo-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole (5.21 g, 0.01 mol), thiophene-3-boronic acid (1.34 g, 0.0105 mol), 250 mL of n-propanol, palladium(II) diacetate (0.090 g, 0.0004 mol), triphenylphosphine (0.315 g, 0.0012 mol), 6 mL of 2M sodium carbonate (1.27 g, 0.012 mol) and 5 mL of water. The residue is purified by dry-column flash chromatography (toluene eluent), followed by recrystallization from heptane to give 4.12 g (78.6% yield) of the title compound as a light yellow solid melting at 147-149° C.

Workup

  1. customThe residue is purified by dry-column flash chromatography (toluene eluent)
  2. customfollowed by recrystallization from heptane

Sources & evidence

ORD record
ord-58634e5f198d4209bbfe954abd8f25db
Source dataset
uspto-grants-2002_05
Patent number
US06387992B1

Reaction notes

Loading…