N,N-Dimethylformamide--water (1/1) → HCID 68458101, compound

HRID 2117358Notes

Reaction equation

HRID 2117358 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[C:22](Br)[CH:23]=[C:18]3[N:17]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].[NH4+].[OH-].O.[CH3:30][N:31](C=O)C.O>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:30]#[N:31])[CH:23]=[C:18]3[N:17]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 59815652HCID 59815652, compoundHCID 86603147HCID 86603147, compound

Product 1

HCID 68458101HCID 68458101, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3-[4-(Benzyloxy)phenyl]-6-bromo-3H-imidazo[4,5-b]pyridine (2 g, 5.26 mmol), Zn(CN)2 (371 mg, 3.16 mmol), Pd2(dba)3 (101 mg, 0.11 mmol) and dppf (122 mg, 0.22 mmol) in degassed DMF/H2O (100:1) (15 mL) was stirred at 120° C. under N2 for 20 h. The mixture was then cooled to rt and treated with NH4Cl:NH4OH:H2O (4:1:4) (45 mL) and reheated to 80° C. for 30 min and then stirred at 0° C. for another 30 min. The precipitated solids were isolated by filtration and purified by chromatography over silica gel eluting with 50% EtOAc/hexane to give 3-[4-(benzyloxy)phenyl]-3H-imidazo[4,5-b]pyridine-6-carbonitrile. 1H NMR (400 MHz, D6-Acetone) δ 5.16 (s, 2H), 7.18 (d, J=8 Hz, 2H), 7.36-7.47 (m, 5H), 7.57 (d, J=8 Hz, 2H), 8.41 (s, 1H), 8.44 (d, J=2 Hz, 1H) and 8.70 (d, J=2 Hz, 1H); MS (ES+): m/z 327 [MH+].

Workup

  1. customThe precipitated solids were isolated by filtration
  2. custompurified by chromatography over silica gel eluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-8af40b4d3ac14099a017f9a0acb45e5d
Source dataset
uspto-grants-2008_10
Patent number
US07442709B2

Reaction notes

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