2-Bromobenzonitrile → 3'-[6-(Furan-3-yl)imidazo[4,5-b]pyridin-3-yl]biphenyl-2-carbonitrile

HRID 2086087Notes

Reaction equation

HRID 2086087 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]3[N:14]=[CH:13][N:12]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17](B5OC(C)(C)C(C)(C)O5)[CH:16]=4)[C:9]3=[N:10][CH:11]=2)=[CH:2]1.Br[C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[C:33]#[N:34].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.ClCCl.CO.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>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]3[N:14]=[CH:13][N:12]([C:15]4[CH:16]=[C:17]([C:31]5[C:32]([C:33]#[N:34])=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH:18]=[CH:19][CH:20]=4)[C:9]3=[N:10][CH:11]=2)=[CH:2]1

Participants

8

Reactant 3

HCID 162722-BromobenzonitrileHCID 62657Potassium Phosphate, TribasicHCID 227279576-(furan-3-yl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3H-imidazo[4,5-b]pyridine

Product 1

HCID 227279593'-[6-(Furan-3-yl)imidazo[4,5-b]pyridin-3-yl]biphenyl-2-carbonitrileYield 39%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A degassed mixture of crude 6-(furan-3-yl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3H-imidazo[4,5-b]pyridine (85 mg), 2-bromobenzonitrile (54 mg, 0.3 mmol), tetrakis(triphenylphosphine)palladium(0) (10 mg) and potassium phosphate (85 mg, 0.4 mmol) in N,N-dimethylformamide (1.5 ml) was heated at 80° C. for 16 hours. The reaction was cooled to ambient temperature, diluted with dichloromethane (10 ml) and methanol (10 ml) and pre-adsorbed onto silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/concentrated ammonia (96:3.5:0.5) furnished the title compound as a cream-coloured solid (31 mg). This was converted to its oxalate salt and crystallised from hot ethanol; δH (400 MHz, d6-DMSO) 7.16-7.17 (1H, m), 7.66 (1H, td, J 8 and 1), 7.70-7.72 (1H, m), 7.78-7.81 (3H, m), 7.87 (1H, td, J 8 and 1), 8.02 (1H, dd, J 8 and 1), 8.17-8.19 (1H, m), 8.25-8.26 (1H, m), 8.36 (1H, s), 8.51 (1H, d, J 2), 8.78 (1H, d, J 2), 9.02 (1H, s); m/z (ES+) 363 (M++H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customPurification by silica gel chromatography
  3. washeluting with dichloromethane/methanol/concentrated ammonia (96:3.5:0.5)

Sources & evidence

ORD record
ord-e79a5d633a02475da029a8caa22f4a31
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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