HCID 178418546, compound → HCID 178437440, compound

HRID 1029586Notes

Reaction equation

HRID 1029586 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][N:29]=[N:28][N:27]=4)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1.[C:32]([Cu])#[N:33]>N1C=CC=CC=1>[C:32]([C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][N:29]=[N:28][N:27]=4)=[CH:18][CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1)#[N:33]

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178437403HCID 178437403, compound

Product 1

HCID 178437440HCID 178437440, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-bromo-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (41 mg), CuCN (80 mg), and pyridine (0.2 mL) was heated with stirring to 160° C. for 4 hours. The pyridine distilled off during the course of the heating. The cooled dark mass was dissolved in 2 mL of 20% aqueous KCN by heating to 50° C. for 15 minutes. Acetic acid (2 mL) (Caution! HCN is evolved.) was added and the mixture was extracted (2×EtOAc). The organic layers were dried (Na2SO4), concentrated, and purified (SiO2, 80/20/1 CH2Cl2 --MeOH--NH4OH) to give 26 mg of the title compound as a solid. 1H NMR (250 MHz, CD3OD) δ7.66-7.45 (m, containing a singlet at 7.57, 5H), 7.15-7.04 (m, 4H), 5.53 (s, 2H), 2.91 (q, 2H, J=7.5 Hz), 2.66 (s, 3H), 1.27 (t, 3H, J=7.5 Hz).

Workup

  1. temperaturewas heated
  2. distillationThe pyridine distilled off during the course of the heating
  3. dissolutionThe cooled dark mass was dissolved in 2 mL of 20% aqueous KCN
  4. temperatureby heating to 50° C. for 15 minutes
  5. additionAcetic acid (2 mL) (Caution! HCN is evolved.) was added
  6. extractionthe mixture was extracted (2×EtOAc)
  7. dry with materialThe organic layers were dried (Na2SO4)
  8. concentrationconcentrated
  9. custompurified (SiO2, 80/20/1 CH2Cl2 --MeOH--NH4OH)

Sources & evidence

ORD record
ord-4bee564551ad4c1797d3dad27ca0d0c7
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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