Sodium Carbonate → HCID 87669248, compound

HRID 925070Notes

Reaction equation

HRID 925070 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1.[CH:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC.O.C(O)C>[O:16]=[C:9]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:20]=[O:21])[CH:27]=3)[CH:19]=[CH:18][CH:17]=2)=[N:7][NH:8]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 59755769HCID 59755769, compound

Product 1

HCID 87669248HCID 87669248, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of EXAMPLE 90 (500 mg, 1.57 mmol), 3-formylphenylboronic acid (352 mg, 2.35 mmol), dichlorobis(triphenylphosphine)palladium(II) (112 mg, 0.16 mmol) and sodium carbonate (2M solution, 3.13 mmol, 1.6 mL) in a 7/3/3 mixture of 1,2-dimethoxyethane/water/ethanol (23 mL) was purged with nitrogen, and heated at 70° C. for 16 hours. After cooling to room temperature, the reaction mixture was concentrated on a rotary evaporator. The crude solid was separated by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0.1% trifluoroacetic acid/CH3CN/H2O) to provide the title compound. MS (DCI/NH3) m/z 345 (M+H)+.

Workup

  1. customwas purged with nitrogen
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated on a rotary evaporator
  4. customThe crude solid was separated by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0.1% trifluoroacetic acid/CH3CN/H2O)

Sources & evidence

ORD record
ord-7b1fe678299d45aaa0d85b2e5fc7bbc3
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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