Sodium Carbonate → HCID 44540690, compound

HRID 1616001Notes

Reaction equation

HRID 1616001 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)=[O:15])[CH:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH:33]=[CH:34][NH:35]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>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].O1CCOCC1>[CH2:11]([N:8]1[C:9]2[C:5](=[C:4]([NH:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[O:15])[CH:3]=[C:2]([C:31]3[CH:39]=[CH:38][CH:37]=[C:36]4[C:32]=3[CH:33]=[CH:34][NH:35]4)[CH:10]=2)[CH:6]=[N:7]1)[CH3:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 58268025HCID 58268025, compound

Product 1

HCID 44540690HCID 44540690, compoundYield 45.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

N-(6-Bromo-1-ethyl-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamide (50 mg, 0.14 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (available from Frontier Scientific, 38 mg, 0.17 mmol), Pd(dppf)Cl2 (23 mg), aqueous sodium carbonate (2M, 0.272 ml) and 1,4-dioxane (2 ml) were combined and heated at 150° C. for 10 mins under microwave conditions. The reaction was extracted into DCM (2×20 ml) and the combined organic layers were evaporated to dryness, before purification by Mass Directed Automated Preparative HPLC (Method B). Pure fractions were evaporated to give the title compound (25 mg).

Workup

  1. extractionThe reaction was extracted into DCM (2×20 ml)
  2. customthe combined organic layers were evaporated to dryness, before purification by Mass Directed Automated Preparative HPLC (Method B)
  3. customPure fractions were evaporated

Sources & evidence

ORD record
ord-8afcf81c800b4dc8b2bbb2a744e9423d
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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