Cesium carbonate → HCID 11710921, compound

HRID 33921Notes

Reaction equation

HRID 33921 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1>CN(C=O)C>[CH3:1][C:2]1[O:3][C:4]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 135988008HCID 135988008, compound

Product 1

HCID 11710921HCID 11710921, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-methyl-5-(pyridin-4-yl)oxazol-4-yl)phenol (21 mg, 0.083 mmol) in 2.5 mL of dry DMF was added Cs2CO3 (54 mg, 0.17 mmol). After stirring for 0.5 h, 2- (chloromethyl)quinoline (17.8 mg, 0.100 mmol) was added and the mixture was stirred at 85° C. for 12 h. After removal of the DMF under vacuum, the residue was purified by PTLC (1:2 hexane/EtOAc) to give 13 mg (40%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ: 2.54 (s, 3H), 5.41 (s, 2H), 7.06 (m, 2H), 7.41 (m, 2H), 7.53 (m, 3H), 7.68 (d, 1H), 7.80 (t, 1H), 7.83 (d, 1H), 8.05 (d, 1H), 8.20 (d, 1H), 8.53 (m, 2H). MS m/z: 394 [M+1]+.

Workup

  1. stirringthe mixture was stirred at 85° C. for 12 h
  2. customAfter removal of the DMF under vacuum
  3. customthe residue was purified by PTLC (1:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-0929307988c04bb29610fc6dda140341
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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