Sodium Carbonate → HCID 21192478, compound

HRID 1067227Notes

Reaction equation

HRID 1067227 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 21192438BECTWGZDTRBAKT-UHFFFAOYSA-N

Product 1

HCID 21192478HCID 21192478, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,7-dibromoisoquinoline (556 mg, 1.93 mmol), tetrakis(triphenylphosphine)-palladium(0) (73 mg, 3 mol %), phenylboronic acid (238 mg, 1.95 mmol), and aqueous sodium carbonate (Na2CO3) (3.9 mL, 1.0 M, 3.9 mmol) in DME (12 mL) was heated at reflux under nitrogen for 20 h. The mixture was diluted with ethyl acetate (EtOAc) (100 mL), washed with water (30 mL), dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (95:5 to 80:20) as eluant to give 4-bromo-7-phenylisoquinoline (389 mg, 1.37 mmol) as a straw-colour solid; 1H (δ, CDCl3, 300 MHz) 7.4-7.6 (3H, m), 7.65-7.75 (2H, m), 8.1 (1H, d), 8.15 (1H, s), 8.2 (1H, d), 8.7 (1H, s), 9.2 (1H, s); LRMS 283, 284, 286.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 20 h
  3. washwashed with water (30 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-986a413ea18442aab2d7f36c63de5128
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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