1H-Indazol-6-amine → HCID 178420055, compound

HRID 1470354Notes

Reaction equation

HRID 1470354 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:3]=12.[NH2:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][NH:24]2)=[CH:20][CH:19]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:24]1[NH:23][CH:22]=[C:21]2[C:25]=1[CH:26]=[C:18]([NH:17][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[O:10][C:3]=13)[CH:19]=[CH:20]2

Participants

7

Reactant 4

HCID 814231H-Indazol-6-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 667792417-Chloro-2-phenyl-furo[3,2-b]pyridine

Product 1

HCID 178420055HCID 178420055, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a 10 mL sealed tube with stirbar was added 7-chloro-2-phenylfuro[3,2-b]pyridine (50.00 mg; 0.22 mmol; 1.00 eq.), 6-aminoindazole (34.79 mg; 0.26 mmol; 1.20 eq.), palladium(II) acetate (2.44 mg; 0.01 mmol; 0.05 eq.), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (10.38 mg; 0.02 mmol; 0.10 eq.), and sodium tert. butoxide (62.77 mg; 0.65 mmol; 3.00 eq.). The reagents were suspended in dioxane (2.00 ml) under a N2 atmosphere and stirred at 110° C. overnight. The reaction mixture was cooled to room temperature and concentrated on a rotary evaporator. The crude mixture was purified by Biotage chromatography (0-10% MeOH/CH2Cl2, 30 column vol) to afford the title compound as a brown solid (6.6 mg, 9%). (HPLC (method F): 97%, RT: 3.97 min); MS (m/z) 327 [M+H]+, RT: 2.6 min.

Workup

  1. customTo a 10 mL sealed tube with stirbar
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated on a rotary evaporator
  4. customThe crude mixture was purified by Biotage chromatography (0-10% MeOH/CH2Cl2, 30 column vol)

Sources & evidence

ORD record
ord-43deb859e1f0476b81e65b715490d7d7
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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