Sodium Carbonate → HCID 70311941, compound

HRID 2038385Notes

Reaction equation

HRID 2038385 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[N:10][C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=1.[C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)#[N:27]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([C:20]1[CH:19]=[C:18]([C:9]2[N:10]=[C:11]([C:13]([OH:15])=[O:14])[S:12][C:8]=2[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([C:26]#[N:27])[CH:33]=2)[CH:23]=[CH:22][CH:21]=1)#[N:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 70801736HCID 70801736, compound

Product 1

HCID 70311941HCID 70311941, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, 3.0 ml of an aqueous 2M sodium carbonate solution and 41.1 mg (0.036 mmol) of tetrakis(triphenylphosphine)palladium are added to 400 mg (1.19 mmol) of the compound from Example 35A and 261 mg (1.78 mmol) of (3-cyanophenyl)boronic acid in 15 ml of DME, and the mixture is subsequently stirred at 80° C. overnight. The crude product is filtered through a short kieselguhr column and the filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography (mobile phase: dichloromethane). 104 mg (26% of theory) of the title compound are obtained.

Workup

  1. filtrationThe crude product is filtered through a short kieselguhr column
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by flash chromatography (mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-20263113f9ed42cab8d985c7fa869c59
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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