Triethylamine → HCID 178498759, compound

HRID 908247Notes

Reaction equation

HRID 908247 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[NH:18][C:12]2=[N:13][CH:14]=[C:15](Br)[CH:16]=[C:11]2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC>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].CO>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[NH:18][C:12]2=[N:13][CH:14]=[C:15]([C:6]([O:5][CH3:1])=[O:19])[CH:16]=[C:11]2[N:10]=1)=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178453114HCID 178453114, compound

Product 1

HCID 178498759HCID 178498759, compoundYield 160.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a MeOH 25 mL solution of tert-butyl[(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)methyl]carbamate (Priepke, H.; Pfau, R; Gerlach, K.; Gillard, J.; Bauer, E.; Wienen, E.; Wolfgang, H.; Sandra N. H. WO 2004056784, 2004.) (1.2 g, 3.66 mmol) were added Et3N (1.11 g, 11 mmol), Pd(dppf)Cl2 (263 mg, 0.366 mmol). The reaction mixture was stirred at 80° C. under CO atmosphere (50 psi) for 24 hr. The reaction mixture was cooled to room temperature, filtered and the filtrate was concentrated, chromatographed on silica gel eluting with DCM: MeOH: TEA (50:1:0.01, v/v/v) to give the title compound (0.9 g, 82%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customchromatographed on silica gel eluting with DCM: MeOH: TEA (50:1:0.01, v/v/v)

Sources & evidence

ORD record
ord-c893dc90c9e84fe2baf45d4eb0ac00dc
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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