Sodium Carbonate → HCID 57682691, compound

HRID 494288Notes

Reaction equation

HRID 494288 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][N:13]=[CH:14]3)=[O:7])=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOC(C)=O.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>[CH:14]1[C:15]2[C:10](=[C:9]([NH:8][C:6]([C:5]3[CH:19]=[CH:20][C:2]([C:26]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:21])[CH:27]=4)=[CH:3][CH:4]=3)=[O:7])[CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:12][N:13]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 8763081HCID 8763081, compound

Product 1

HCID 57682691HCID 57682691, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N-isoquinolin-5-ylbenzamide (D94) (50 mg, 0.153 mmol) in toluene (2 ml) and ethanol (0.4 ml) under an argon atmosphere was added 3-methyl-phenylboronic acid (21 mg, 0.153 mmol), 2M sodium carbonate solution (0.15 ml) and tetrakis(triphenylphosphine)palladium (0) (5 mg, 0.05 mmol). The reaction was heated at reflux for 18 h, then cooled to room temperature and diluted with EtOAc. The mixture was washed with sat. aq. sodium bicarbonate solution and water, dried over MgSO4 and concentrated to give the crude product which was purified by SPE column chromatography. Elution with 50% EtOAc/40-60° C. petroleum ether gave the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.32 (s, 1H), 8.62 (d, 1H), 8.34 (d, 1H), 8.22 (br, 1H), 8.07 (d, 2H), 7.90, (d, 1H), 7.78 (d, 2H), 7.70 (m, 3H), 7.47 (m, 2H), 7.40 (t, 1H), 2.47 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. washThe mixture was washed with sat. aq. sodium bicarbonate solution and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by SPE column chromatography
  8. washElution with 50% EtOAc/40-60° C. petroleum ether

Sources & evidence

ORD record
ord-ca2f65c28c5c459b952468aac222181f
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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