Cesium carbonate → HCID 57503085, compound

HRID 2353572Notes

Reaction equation

HRID 2353572 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:12]2=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=[C:11]2[N:10]=1.ClC1N=C2N([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)C(=O)NC2=CC=1.C1C2CC(Br)C(C2)C1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:37]12[CH2:43][CH:40]([CH2:39][CH2:38]1)[CH2:41][CH:42]2[N:10]1[C:11]2[C:12](=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:9]1=[O:8].[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[C:12]2=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=[C:11]2[N:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 982322-Norbornyl bromideHCID 57418557HCID 57418557, compoundHCID 57503084HCID 57503084, compound

Product 2

HCID 57503084HCID 57503084, compoundYield 9%HCID 57503085HCID 57503085, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

1-Bicyclo[2.2.1]hept-2-yl-5-chloro-3-p-tolyl-13-dihydro-imidazo[4,5-b]pyridine-2-one (38) and 2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine (39). A mixture of 5-Chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one (52 mg, 0.2 mmol), exo-2-bromonorbornane (103 μL, 0.8 mmol) and Cs2CO3 (195 mg, 0.6 mmol) in 1.5 mL DMF was heated in microwave at 200° C. for 20 min. After filtration, the filtrate was diluted with EtOAc, washed with water. The organic phase was concentrated, the residue was dissolved in a minimum amount of DCM, and subjected to silica gel column purification to give 21.2 mg (yield: 30%) 1-Bicyclo[2.2.1]hept-2-yl-5-chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one (Rf=0.60 in DCM) and 6.2 mg (yield: 9%) 2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine (Rf=0.49 in DCM). Calculated mass=353. Observed mass=354.

Workup

  1. filtrationAfter filtration
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with water
  4. concentrationThe organic phase was concentrated
  5. dissolutionthe residue was dissolved in a minimum amount of DCM
  6. customsubjected to silica gel column purification

Sources & evidence

ORD record
ord-e25e05e4ae064bf99f7448f72b9753ff
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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