Cesium carbonate → HCID 70498648, compound

HRID 1045503Notes

Reaction equation

HRID 1045503 reaction equation
Cl[C:2]1[C:11]2[CH2:10][N:9]([CH2:12][CH3:13])[C:8](=[O:14])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26]3=[N:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=4)[CH:30]=[C:25]3[CH:24]=[CH:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:12]([N:9]1[CH2:10][C:11]2[C:2]([O:37][C:34]3[CH:33]=[CH:32][C:31]([C:29]4[CH:30]=[C:25]5[CH:24]=[CH:23][N:22]([C:19]6[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=6)[C:26]5=[N:27][CH:28]=4)=[CH:36][CH:35]=3)=[CH:3][CH:4]=[N:5][C:6]=2[NH:7][C:8]1=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70497722HCID 70497722, compoundHCID 70498216HCID 70498216, compound

Product 1

HCID 70498648HCID 70498648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 10-mL microwave vial equipped with a stir-bar was added 5-chloro-3-ethyl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one (30.00 mg; 0.14 mmol), 4-[1-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]phenol (64.70 mg; 0.21 mmol) and cesium carbonate (138.55 mg; 0.43 mmol). The mixture was suspended in DMF (2.00 ml). The vial was then loaded onto the microwave reactor and run at 160° C. for 2 h. The reaction mixture was filtered through a bed of silica under reduced pressure. The crude material was purified via Biotage eluting with a gradient of 50 to 100% EtOAc in Hexanes to provide 275 as an off-white solid. LC-MS (M+H=480, obsd.=480). 1H-NMR: (DMSO-D6) δ 9.66 (s, 1H); 8.64 (d, 1H); 8.37 (d, 1H); 7.97 (m, 4H); 7.84 (d, 2H); 7.41 (t, 2H); 7.30 (d, 2H), 6.78 (d, 1H); 6.27 (d, 1H); 4.54 (s, 2H); 3.40 (q, 2H); 1.11 (t, 3H).

Workup

  1. customInto a 10-mL microwave vial equipped with a stir-bar
  2. filtrationThe reaction mixture was filtered through a bed of silica under reduced pressure
  3. customThe crude material was purified via Biotage
  4. washeluting with a gradient of 50 to 100% EtOAc in Hexanes

Sources & evidence

ORD record
ord-a13bfcf4ae844676ac54a34f68087778
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

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