(3-Ethoxycarbonylphenyl)boronic acid → HCID 68234204, compound

HRID 876890Notes

Reaction equation

HRID 876890 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:21])[CH3:18]>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]>[CH:14]1([C:12]([NH:11][C:6]2[C:5]3[C:9](=[CH:10][C:2]([C:26]4[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=4)[C:20]([O:19][CH2:17][CH3:18])=[O:21])=[CH:3][CH:4]=3)[NH:8][N:7]=2)=[O:13])[CH2:16][CH2:15]1

Participants

6

Reactant 2

HCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 67387672HCID 67387672, compound

Product 1

HCID 68234204HCID 68234204, compoundYield 80.1%

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-(6-bromo-1H-indazol-3-yl)cyclopropanecarboxamide (560 mg, 2.0 mmol) in dioxane (20 mL) and 1N sodium carbonate solution (8 mL) were added 3-(ethoxycarbonyl)phenylboronic acid (388 mg, 2.0 mmol) and Pd(dppf)Cl2 (103 mg, 0.2 mmol). 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 flash chromatography with 20:1 (v/v) methylene chloride-methanol to afford the title product (560 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 flash chromatography with 20:1 (v/v) methylene chloride-methanol

Sources & evidence

ORD record
ord-9fd0b04fad6d45768155bf60b113f3f5
Source dataset
uspto-grants-2015_03
Patent number
US08987275B2

Reaction notes

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