Sodium Carbonate → HCID 59423930, compound

HRID 500622Notes

Reaction equation

HRID 500622 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]#[N:17])[CH2:8]1.[OH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:35][C:36]1[CH:41]=[C:40]([C:2]2[CH:34]=[CH:33][CH:32]=[C:4]([CH2:5][O:6][C@H:7]3[CH2:11][CH2:10][N:9]([C:12]([CH3:30])([CH3:31])[CH2:13][CH2:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]#[N:17])[CH2:8]3)[CH:3]=2)[CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59423922HCID 59423922, compound

Product 1

HCID 59423930HCID 59423930, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (16 mg, 19 μmol) was added to a solution of the product of example 55 (205 mg, 0.38 mmol), 3-hydroxyphenylboronic acid (106 mg, 0.77 mmol) and sodium carbonate (81 mg, 0.77 mmol) in tetrahydrofuran (5 mL) and water (1 mL) and the mixture was heated under reflux for 16 hours. The cooled reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate:methanol, 98:2 to 96:4, to afford the title compound in 25% yield, 51 mg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4baec0792df945cb9891b9f24df9689b
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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