HCID 67383044, compound → HCID 70682038, compound

HRID 876892Notes

Reaction equation

HRID 876892 reaction equation
[CH3:1][NH:2][C:3]1[C:11]2[C:6](=[CH:7][C:8](B3OC(C)(C)C(C)(C)O3)=[CH:9][CH:10]=2)[NH:5][N:4]=1.[CH2:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[C:40](I)[CH:39]=3)=[CH:32][C:31]=2[C:46]([F:49])([F:48])[F:47])[CH2:25][CH2:24]1)[CH3:22]>O1CCOCC1.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]>[CH2:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:8]4[CH:7]=[C:6]5[C:11]([C:3]([NH:2][CH3:1])=[N:4][NH:5]5)=[CH:10][CH:9]=4)[CH:39]=3)=[CH:32][C:31]=2[C:46]([F:49])([F:47])[F:48])[CH2:25][CH2:24]1)[CH3:22]

Participants

6

Reactant 2

HCID 67383044HCID 67383044, compoundHCID 67386790HCID 67386790, compound

Product 1

HCID 70682038HCID 70682038, compoundYield 18.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-amine (14 mg, 0.05 mmol) in dioxane (1.25 mL) and 1N sodium carbonate solution (0.25 mL) were added N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-iodobenzamide (26 mg, 0.05 mmol) and Pd(dppf)Cl2 (4 mg, 5 μmol). After the reaction was stirred at 100° C. for 4 hours and cooled to room temperature, the mixture was filtered through Celite and washed by ethyl acetate. The combined organic solution was washed by brine, dried with sodium sulfate and concentrated in vacuo. The crude residue was purified by HPLC to afford the title product (4.9 mg).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. washwashed by ethyl acetate
  4. washThe combined organic solution was washed by brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by HPLC

Sources & evidence

ORD record
ord-c084c594f16347aeb529c62b4ba48fec
Source dataset
uspto-grants-2015_03
Patent number
US08987275B2

Reaction notes

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