Sodium Carbonate → HCID 24801481, compound

HRID 469814Notes

Reaction equation

HRID 469814 reaction equation
Br[C:2]1[C:7]2[O:8][C:9]([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:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=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>[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:7]3[O:8][C:9]([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:10][C:6]=3[CH:5]=[CH:4][N:3]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346154-Aminophenylboronic acidHCID 86637873HCID 86637873, compound

Product 1

HCID 24801481HCID 24801481, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

0.082 g (0.209 mmol) (4-bromo-oxazolo[5,4-c]pyridin-2-yl)-(3,4,5-trimethoxy-phenyl)-amine and 0.04 g (0.22 mmol) (4-aminophenyl) boronic acid are dissolved in 3 ml 1,2-dimethoxy-ethane, a solution of 0.044 g (0.425 mmol) Na2CO3 (in 0.6 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 (0.0259 g, 0.021 mmol) is added and the reaction mixture is stirred at 100° C. or 83 h. After that the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane=>EtOAc) and recrystallisation from dichloromethane/diethyl ether to afford the title compound. Rt=1.70 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: 393 (M+1)+; m.p. 148-151° 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 and saturated NaCl solution
  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) and recrystallisation from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-8c665b4d56674fba82cf49fbdd764619
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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