5-isopropyl-1-methyl-3-(tributylstannyl)-1H-indazole → (7-(tert-butylcarbamoyl)-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate

HRID 246769Notes

Reaction equation

HRID 246769 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[N:8]=[C:7]2[Sn](CCCC)(CCCC)CCCC)([CH3:3])[CH3:2].[C:27]([O:33][CH2:34][N:35]1[C:39]2=[N:40][CH:41]=[C:42](Br)[N:43]=[C:38]2[C:37]([C:45](=[O:51])[NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:36]1)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C.[Cu]I.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>[C:27]([O:33][CH2:34][N:35]1[C:39]2=[N:40][CH:41]=[C:42]([C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=4)[N:9]([CH3:13])[N:8]=3)[N:43]=[C:38]2[C:37]([C:45](=[O:51])[NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:36]1)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 2

HCID 712803365-isopropyl-1-methyl-3-(tributylstannyl)-1H-indazoleHCID 86677996(2-bromo-7-(tert-butylcarbamoyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate

Product 1

HCID 71279754(7-(tert-butylcarbamoyl)-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture 5-isopropyl-1-methyl-3-(tributylstannyl)-1H-indazole, (2-bromo-7-(tert-butylcarbamoyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (0.408 g, 1 mmol), CuI (0.06 g, 0.32 mmol) and Pd(PPh3)4 (0.06 g, 0.052 mmol) in 40 mL of DMF was stirred at 80° C. under nitrogen for 4 hours. The solvent was removed under reduced pressure and the residue was triturated with water (15 mL) and petroleum ether (30 mL) then decanted and dried to give crude (7-(tert-butylcarbamoyl)-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (0.15 g) as a yellow solid, which was used into next step without further purification. LCMS: (M+H)+=505.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with water (15 mL) and petroleum ether (30 mL)
  3. customthen decanted
  4. customdried

Sources & evidence

ORD record
ord-dfbfe25959414b4080d3f4f04b9697b6
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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