Ammonium Chloride → Bnc-105

HRID 1191990Notes

Reaction equation

HRID 1191990 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23](OC)[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[CH3:31]B(O)O.[C:35](=[O:38])(O)[O-].[Na+].[Cl-].[NH4+]>O1CCOCC1.O.ClCCl>[CH3:31][C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:38][CH3:35])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 139377Methylboronic AcidHCID 516892Sodium BicarbonateHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 24786555Bnc-105

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran (20 mg, 0.042 mmol), methyl-boronic acid (40 mg, 0.67 mmol), in 1,4-dioxane (2 mL) at 90° C. was added tetrakis-triphenylphosphine palladium (11 mg, 0.01 mmol) followed by the addition of a solution of sodium bicarbonate (40 mg, 0.48 mmol) in distilled water (0.5 mL). The reaction mixture turned red after 5 minutes. After 2 hours (tlc) the reaction mixture was brought to room temperature and was added saturated ammonium chloride (2 mL) and diluted with dichloromethane (20 mL). The organic layer was separated and washed with water, dried over magnesium sulfate and the solvent was removed by distillation under vacuum. The residue was purified by PTLC (eluent=Dichloromethane/Methanol, 1:1) to give the title compound (actate cleaved during reaction) as a fluffy white solid; (3 mg, 19%).

Workup

  1. waitAfter 2 hours (tlc) the reaction mixture was brought to room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by distillation under vacuum
  6. customThe residue was purified by PTLC (eluent=Dichloromethane/Methanol, 1:1)

Sources & evidence

ORD record
ord-70e37ec6a3d049c58d016ea394d684fa
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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