Potassium Carbonate → 5-Bromo-1-(3-methoxy-phenyl)-1H-indazole

HRID 333847Notes

Reaction equation

HRID 333847 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[C:11]([O-:14])([O-])=O.[K+].[K+].C[NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1NC.C[N:28]1CCCC1=O>[Cu]I.CN[C@@H]1CCCC[C@H]1NC>[Br:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:14][CH3:11])[CH:20]=1)[N:28]=[CH:4]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 135400692,5-Dibromobenzaldehyde

Product 1

HCID 574213495-Bromo-1-(3-methoxy-phenyl)-1H-indazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineCatalyst

Conditions

Temperature
160 °C

Procedure

3-Methoxyphenylhydrazine hydrochloride (1 g) was suspended in 1M aqueous NaOH solution and extracted with ether. The organic phase was dried (MgSO4), filtered and concentrated to dryness to give 3-methoxyphenylhydrazine. 2,5-Dibromobenzaldehyde (1 g) and N-methylpyrrolidone (3.7 ml) were added and the mixture was heated under microwave conditions to 160° C. for 10 min. K2CO3 (1.015 g), CuI (36 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (53 mg) were added and the mixture was heated under microwave conditions to 160° C. for 40 min. CuI (18 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (26 mg) were added and the mixture was heated under microwave conditions to 160° C. for 20 min. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, CH2Cl2/MeOH 100:0=>95:5) to give the title compound (659 mg) as a yellow oil. MS (m/e)=303.0 [M+H+].

Workup

  1. temperaturethe mixture was heated under microwave conditions to 160° C. for 40 min
  2. temperaturethe mixture was heated under microwave conditions to 160° C. for 20 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe product was purified by chromatography (SiO2, CH2Cl2/MeOH 100:0=>95:5)

Sources & evidence

ORD record
ord-36eaf112e4774505aaeff684bd6c569b
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

Loading…