Potassium Carbonate → HCID 59320248, compound

HRID 655275Notes

Reaction equation

HRID 655275 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)=[CH:15]4)=[N:9][N:10]=2)[N:7]=1.[CH:28](B1OC(C)(C)C(C)(C)O1)=[CH2:29].C(=O)([O-])[O-].[K+].[K+]>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]>[CH3:27][N:25]1[CH:26]=[C:22]([C:16]2[CH:17]=[N:18][C:19]3[C:14]([CH:15]=2)=[CH:13][C:12]([CH2:11][C:8]2[N:6]4[N:7]=[C:2]([CH:28]=[CH2:29])[CH:3]=[CH:4][C:5]4=[N:10][N:9]=2)=[CH:21][CH:20]=3)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59320311HCID 59320311, compound

Product 1

HCID 59320248HCID 59320248, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Conditions

Temperature
135 °C

Procedure

To a degassed (bubbled nitrogen for 15 mins) mixture of water (1 mL) and 1,4-dioxane (2 mL) was added 6-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-(1-methyl-1H-pyrazol-4-yl)-quinoline (117 mg, 0.31 mmol), vinyl boronic acid pinacol ester (59 μl, 0.35 mmol), potassium carbonate (0.93 mmol, 128 mg) and dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (15 mg, 0.02 mmol). The microwave tube was capped and heated in a microwave reactor (Personel Chemistry, Emrys Optimizer) at 135° C. for 1500 seconds. After such time the organic phase was concentrated on silica and purified via flash column chromatography eluting with 0-10% Methanol in dichloromethane to obtain the title compound (22 mgs, 19% yield) as a white solid. Analytical data presented in Table 2.

Workup

  1. customTo a degassed
  2. custom(bubbled nitrogen for 15 mins) mixture of water (1 mL) and 1,4-dioxane (2 mL)
  3. customThe microwave tube was capped
  4. concentrationAfter such time the organic phase was concentrated on silica
  5. custompurified via flash column chromatography
  6. washeluting with 0-10% Methanol in dichloromethane

Sources & evidence

ORD record
ord-b76512399cd041c0b4dca274fadbf03e
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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