Sodium Carbonate → HCID 22241318, compound

HRID 892165Notes

Reaction equation

HRID 892165 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[N:16]=[C:15]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:36]=[CH:37][CH:38]=2)[O:22][CH2:23][C:24]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:25]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(C#N)(C)=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:24]([CH2:23][O:22][C:21]2[CH:36]=[CH:37][CH:38]=[C:19]([O:18][CH2:17][C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:16]=3)[CH:20]=2)[C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 694302-OxopropiononitrileHCID 22241522HCID 22241522, compound

Product 1

HCID 22241318HCID 22241318, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of phenylboronic acid (74.0 mg, 0.607 mmoles), ethyl 2-[3-(6-chloropyridin-2-ylmethoxy)-phenoxymethyl]-6-methylbenzoate (250 mg, 0.607 mmoles, example 6v), and sodium carbonate (77.8 mg, 1.21 mmoles) in 1:1H2O:AcCN (8 mL) is stirred under vacuum for five minutes. The reaction is placed under nitrogen, and tetrakis(triphenylphosphine)-palladium(0) (60.7 mg) is added followed by heating to 90° C. After two hours, another portion (15 mg) of phenylboronic acid is added. After another hour heating is stopped. Distilled water (10 mL) is added, followed by extraction with methylene chloride (twice with 20 mL). The organic extracts are combined and concentrated, and the resulting residue is purified by column chromatography (silica, 6:1 hex:EtOAc) to yield the title compound. MS (ESI) 454 (M+H)+.

Workup

  1. temperatureAfter another hour heating
  2. extractionfollowed by extraction with methylene chloride (twice with 20 mL)
  3. concentrationconcentrated
  4. customthe resulting residue is purified by column chromatography (silica, 6:1 hex:EtOAc)

Sources & evidence

ORD record
ord-71d738673d9d4f1fb51b63080396d761
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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