Sodium Carbonate → HCID 44547058, compound

HRID 402101Notes

Reaction equation

HRID 402101 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.Br[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[N:17][CH:16]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][N:17]1[CH2:16][CH:15]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 737434-BromoisoquinolineHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 44547058HCID 44547058, compoundYield 447.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Naphthaleneboronic acid (1.2 g, 7.2 mmol) was added to a solution of 4-bromoisoquinoline (1.0 g, 4.8 mmol) and triphenylphosphine (0.3 g, 0.9 mmol) in 1,2-dimethoxyethane (10 ml). The mixture was degassed with argon. Palladium(II) acetate (0.1 g, 0.5 mmol) was added and the suspension was stirred at room temperature for 20 minutes. Aqueous sodium carbonate (5.8 ml, 2 M) was added and the suspension was degassed with argon. After stirring at 85° C. for 3 hours, the cooled mixture was diluted with water and extracted with dichloromethane once. The combined extracts were dried with sodium sulfate, concentrated under vacuum and purified by chromatography (5:1 heptane/ethyl acetate) to give the desired product (1.1 g, 90%, 95% AUC GC): 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 8.62 (s, 1H), 7.92-8.12 (m, 6H), 7.56-7.72 (m, 5H).

Workup

  1. customThe mixture was degassed with argon
  2. customthe suspension was degassed with argon
  3. stirringAfter stirring at 85° C. for 3 hours
  4. additionthe cooled mixture was diluted with water
  5. extractionextracted with dichloromethane once
  6. dry with materialThe combined extracts were dried with sodium sulfate
  7. concentrationconcentrated under vacuum
  8. custompurified by chromatography (5:1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a0e10f209e194d0fb39f48ac9f3827ca
Source dataset
uspto-grants-2014_06
Patent number
US08741901B2

Reaction notes

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