Isopropanol → 6-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole

HRID 1615977Notes

Reaction equation

HRID 1615977 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[NH:15]1[C:23]2[C:18](=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.CC(O)C.C(=O)(O)[O-].[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].C(OCC)(=O)C>[NH:15]1[C:23]2[C:18](=[C:19]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=3)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 58267997HCID 58267997, compound

Product 1

HCID 582679906-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazoleYield 43%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

6-Bromo-1-methyl-4-nitro-1H-indazole (100 mg, 0.39 mmol), Pd(dppf)Cl2 (32 mg, 0.04 mmol) and 1H-indol-4-ylboronic acid (94 mg, 0.59 mmol) were treated with a 4:1 mixture of propan-2-ol and saturated sodium bicarbonate solution (3 ml) and the reaction was heated in a microwave at 150° C. for 10 mins. Ethyl acetate was added, a solid was filtered off and the filtrate was partitioned between ethyl acetate and water. The water was washed twice with ethyl acetate and the combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica chromatography, eluting with 0-25% ethyl acetate in cyclohexane. Appropriate fractions were combined and evaporated to give the title compound (49 mg) as an orange solid.

Workup

  1. filtrationa solid was filtered off
  2. customthe filtrate was partitioned between ethyl acetate and water
  3. washThe water was washed twice with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica chromatography
  9. washeluting with 0-25% ethyl acetate in cyclohexane
  10. customevaporated

Sources & evidence

ORD record
ord-5a8cf03d7b0e4feab10b1f4540082b41
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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