Toluene → HCID 19703126, compound

HRID 861418Notes

Reaction equation

HRID 861418 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[OH:19].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(O)C.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[C:13]([OH:19])=[CH:14][CH:15]=[C:16]([CH3:18])[N:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 899572-Iodo-6-methylpyridin-3-ol

Product 1

HCID 19703126HCID 19703126, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-bromobenzeneboronic acid (2.0 g) in ethanol (10 ml) was added over a period of 15 minutes to a stirred mixture of 6-iodo-2-picolin-5-ol (2.35 g), saturated aqueous sodium carbonate solution (5.0 ml), tetrakis(triphenylphosphine)palladium [0] (280 mg) and toluene (10 ml) under an atmosphere of argon. The mixture was stirred at reflux for 6 hours. The mixture was evaporated and the residue was treated with water (20 ml). The mixture was filtered and the yellow solid collected was purified by flash column chromatography on alumina (1CN Biomedicals Alumina N32-63) using 50% n-pentane/ethyl. acetate as eluent to give 2-(4-bromophenyl)-3-hydroxy-6-methylpyridine (600 mg), m.p. 196°-199° C.; NMR: 2.42(3H,s), 7.09(1H,d), 7.25(1H,d), 7.62(2H,d), 8.02(2H,d), 9.98(1H,s); m/z 264 & 266 (M+H).

Workup

  1. temperatureat reflux for 6 hours
  2. customThe mixture was evaporated
  3. additionthe residue was treated with water (20 ml)
  4. filtrationThe mixture was filtered
  5. customthe yellow solid collected
  6. customwas purified by flash column chromatography on alumina (1CN Biomedicals Alumina N32-63)

Sources & evidence

ORD record
ord-b0e3ec097c5e40148ea9cdd37af35459
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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