Sodium Carbonate → HCID 9801001, compound

HRID 1744227Notes

Reaction equation

HRID 1744227 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:5]([NH2:8])=[N:6][CH:7]=1.[O:19]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][NH:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:29]2[CH:30]=[CH:31][C:26]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:27][CH:28]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 10018173HCID 10018173, compound

Product 1

HCID 9801001HCID 9801001, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1.00 eq. of (4) in 1 mL toluene is treated with 10 mole percent tetrakis(triphenylphospine) palladium under nitrogen at room temperature. To this solution is added directly 2.50 eq. of 4-phenoxyphenyl boronic acid at room temperature and then 1 mL Na2CO3 (1.0 M) solution. The reaction vial is capped and the reaction stirred under nitrogen at 90° C. for 10 hours. The toluene layer is separated and removed under reduced pressure, and the resulting oil is purified via flash chromatography to provide (5).

Workup

  1. customThe reaction vial is capped
  2. customThe toluene layer is separated
  3. customremoved under reduced pressure
  4. customthe resulting oil is purified via flash chromatography

Sources & evidence

ORD record
ord-8d4011e919e84d3f9b24c679cbda4cc2
Source dataset
uspto-grants-2006_03
Patent number
US07015227B2

Reaction notes

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