6-bromo-1H-indazol-3-amine → HCID 67387291, compound

HRID 876893Notes

Reaction equation

HRID 876893 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH2:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16])[CH3:13]>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]>[NH2:11][C:6]1[C:5]2[C:9](=[CH:10][C:2]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[C:15]([O:14][CH2:12][CH3:13])=[O:16])=[CH:3][CH:4]=2)[NH:8][N:7]=1

Participants

6

Reactant 2

HCID 27866316-bromo-1H-indazol-3-amineHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

Product 1

HCID 67387291HCID 67387291, compoundYield 51.9%

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 6-bromo-1H-indazol-3-amine (2.1 g, 10.0 mmol) in dioxane (100 mL) and sodium carbonate (1N, 40 mL) were added 3-(ethoxycarbonyl)phenylboronic acid (1.94 g, 10.0 mmol) and Pd(dppf)Cl2 (816 mg, 1.0 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 50:1 (v/v) methylene chloride-methanol to afford the title product (1.46 g), MS m/z: 282.11 (M+1).

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 50:1 (v/v) methylene chloride-methanol

Sources & evidence

ORD record
ord-e79d222a62f6485ebfd8a9ffd77e7250
Source dataset
uspto-grants-2015_03
Patent number
US08987275B2

Reaction notes

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