Cesium carbonate → HCID 57691275, compound

HRID 219178Notes

Reaction equation

HRID 219178 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][O:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=4)[N:16]=[CH:15][CH:14]=3)=[N:9][N:10]=2)[N:7]=1.[Cl:25][C:26]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:37][C:27]=1[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:25][C:26]1[CH:40]=[C:39]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH2:11][O:12][C:13]4[C:22]5[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=5)[N:16]=[CH:15][CH:14]=4)=[N:9][N:10]=3)[N:7]=2)[CH:38]=[CH:37][C:27]=1[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 250669924-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinolineHCID 57691281HCID 57691281, compound

Product 1

HCID 57691275HCID 57691275, compound

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (200 mg, 585 μmol), tert-butyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (323 mg, 878 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(ii) dichloromethane adduct (86 mg, 117 μmol), cesium carbonate (763 mg, 2341 μmol) in dioxane (3 mL) and water (0.3 mL) was sparged with argon for 10 min then heated to 100° C. for 18 h. Reaction then partitioned between 9:1 CHCl3/IPA (50 mL) and 5% NaHCO3 (25 mL). Aqueous further extracted with 9:1 CHCl3/IPA (2×10 mL). Combined organics then dried over MgSO4, concentrated, and purified on silica (40 g) eluting with 0>6% 2M NH3 in MeOH/DCM. Product isolated as an off white solid. 84024-19-2 MS (ESI pos. ion) m/z: 547 (MH+). Calc'd exact mass for C28H27ClN6O4: 546.

Workup

  1. customwas sparged with argon for 10 min
  2. customReaction
  3. customthen partitioned between 9:1 CHCl3/IPA (50 mL) and 5% NaHCO3 (25 mL)
  4. extractionAqueous further extracted with 9:1 CHCl3/IPA (2×10 mL)
  5. dry with materialCombined organics then dried over MgSO4
  6. concentrationconcentrated
  7. custompurified on silica (40 g)
  8. washeluting with 0>6% 2M NH3 in MeOH/DCM
  9. customProduct isolated as an off white solid

Sources & evidence

ORD record
ord-9d759a60105f4eab87bbb8d063c8ee4f
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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