Sodium Carbonate → HCID 24800422, compound

HRID 469802Notes

Reaction equation

HRID 469802 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:24]1([CH3:33])[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.[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>[C:24]1([CH3:33])[CH:29]=[CH:28][CH:27]=[C:26]([C:2]2[C:10]3[O:9][C:8]([NH:11][C:12]4[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=4)=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 67457973HCID 67457973, compound

Product 1

HCID 24800422HCID 24800422, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

0.12 g (0.316 mmol) (7-bromo-benzooxazol-2-yl)-(3,4,5-trimethoxy-phenyl)-amine and 0.048 g (0.353 mmol) 3-tolyl boronic acid are dissolved in 4 ml 1,2-dimethoxy-ethane, a solution of 0.1 g (0.95 mmol) Na2CO3 (in 0.5 ml water) is added and a stream of argon is bubbled through the mixture in order to exclude oxygen from the reaction mixture. Tetrakis (triphenylphosphine) palladium (76 mg, 0.064 mmol) is added and the reaction mixture is stirred at 100° C. or 3 h. After that the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:EtOAc=3:1=>1:1) to afford the title compound as an off-white solid, m.p. 153-155° C. Rt=2.54 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min). MS: 391 (M+1)+; m.p. 155-158° C.

Workup

  1. customa stream of argon is bubbled through the mixture in order
  2. additionAfter that the reaction mixture is poured on water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers are washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by chromatography (silicagel, hexane:EtOAc=3:1=>1:1)

Sources & evidence

ORD record
ord-7cf7a0b496dd4bf9ba7d062e0ce94280
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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