Potassium Carbonate → HCID 67521166, compound

HRID 1926326Notes

Reaction equation

HRID 1926326 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 67521166HCID 67521166, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2-amino-3-bromopyridine (1.0 g, 5.7 mmol), benzofuran-2-boronic acid (1.03 g, 6.4 mmol), Pd(dppf)2Cl2 (50 mg) and K2CO3 (1.83 g, 13.3 mmol) in dioxane/H2O (4:1, 5 under nitrogen at 80° C. for 16 h, cooled to RT, and concentrated in vacuo. The solid residue thus obtained was dissolved in EtOAc (30 mL) and washed with water (20 mL) and dried in vacuo. The crude material was purified by chromatography on silica gel using EtOAc/Hexanes (1:4) to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=5.61 (brs, 2H), 6.82 (dd, J=7.2, 4.1 Hz, 1H), 7.05 (s, 1H), 7.25-7.28 (m, 2H), 7.60 (d, J=7.2 Hz, 1H), 7.66 (d, J=7.2 Hz, 1H), 7.94 (d, J=2.4 Hz, 1H), 8.19 (d, 2.4 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe solid residue thus obtained
  3. washwashed with water (20 mL)
  4. customdried in vacuo
  5. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-06bb6c980b164e7ea3d74f1f0afa8bfb
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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