Sodium Carbonate → HCID 49869079, compound

HRID 450183Notes

Reaction equation

HRID 450183 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:23]([F:25])[F:24])[N:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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]>[F:24][CH:23]([F:25])[C:15]1[N:14]([C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=[C:2]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)[N:3]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 220368724-(4-chloro-6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine

Product 1

HCID 49869079HCID 49869079, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (0.183 g, 0.5 mmol), 3-pyridylboronic acid (92 mg, 0.75 mmol), PdCl2(dppf) (28 mg), and aq. Na2CO3 (2M, 4 mL) in dioxane (20 mL) was heated under reflux under nitrogen for 1 hr. After cooling, the mixture was diluted with water, extracted with CH2Cl2, and dried. Chromatography on alumina, eluting with CH2Cl2, gave 0.13 g (64% yield) of 2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole: mp (MeOH) 199-201° C.; 1H NMR (DMSO-d6) δ 9.59 (d, J=1.6 Hz, 1H), 8.85 (dd, J=4.8, 1.7 Hz, 1H), 8.75 (td, J=8.0, 1.9 Hz, 1H), 8.50 (d, J=8.2 Hz, 1H), 7.90 (d, J=7.9 Hz, 1H), 7.86 (t, JHF=52.6 Hz, 1H), 7.65 (ddd, J=8.0, 4.8, 0.7 Hz, 1H), 7.59 (dt, J=7.8, 1.1 Hz, 1H), 7.49 (dt, J=7.6, 1.1 Hz, 1H), 4.09 (m, 2H), 3.94 (m, 2H), 3.79 (m, 4H); Anal. Calcd. for C20H17F2N7O: C, 58.7; H, 4.2; N, 23.95. Found: C, 58.45; H, 4.1; N, 24.2%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 1 hr
  3. temperatureAfter cooling
  4. extractionextracted with CH2Cl2
  5. customdried
  6. washChromatography on alumina, eluting with CH2Cl2

Sources & evidence

ORD record
ord-1fcac98ae47046cc873265ca8e570c5d
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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