4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester → 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester

HRID 59808Notes

Reaction equation

HRID 59808 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]([CH3:16])[CH3:15])=[C:7](I)[CH:6]=1)=[O:4].[Br-].[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([Zn+])=[N:24][CH:25]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]([CH3:16])[CH3:15])=[C:7]([C:23]2[CH:22]=[CH:21][C:20]([CH3:19])=[CH:25][N:24]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 596277684-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl esterHCID 178427808HCID 178427808, compound

Product 1

HCID 596277651-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl esterYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester (1.13 g, 3.28 mmol) in THF (30 mL) was added Pd(PPh3)4 (0.2 g, 0.164 mmol), followed by 5-methyl-pyridinyl zinc bromide ((19.7 mL of 0.5M solution in THF, 9.86 mmol). The reaction mixture was stirred overnight at room temperature, then quenched by addition of saturated aqueous NH4Cl solution. The mixture was partitioned between water and ethyl acetate, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography gave 0.5 g (50%) of 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester.

Workup

  1. customquenched by addition of saturated aqueous NH4Cl solution
  2. customThe mixture was partitioned between water and ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-1fab89b81674456f9145bd3df70cc8da
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Reaction notes

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