1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → 6-{1-[(4-Methyl phenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridin-5-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 520589Notes

Reaction equation

HRID 520589 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn](C)(C)C)[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:25]1[CH:26]=[C:27]2[CH:33]=[N:32][N:31]([S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:28]2=[N:29][CH:30]=1>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.CN(C=O)C>[CH3:43][C:40]1[CH:41]=[CH:42][C:37]([S:34]([N:31]2[C:28]3=[N:29][CH:30]=[C:25]([C:16]4[CH:15]=[C:14]([NH2:23])[C:13]5[CH:12]=[N:11][N:10]([S:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)(=[O:9])=[O:8])[C:18]=5[CH:17]=4)[CH:26]=[C:27]3[CH:33]=[N:32]2)(=[O:36])=[O:35])=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amineHCID 666958975-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 666957476-{1-[(4-Methyl phenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridin-5-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1-(Phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (775 mg), Pd(PPh3)4 (212 mg) and 5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridine (775 mg) were introduced into a microwave vial and DMF (10 ml) was added. The mixture was heated in the microwave at 120° C. for 4 h. The solvent was removed in vacuo and the crude residue was placed on a high vacuum line overnight. The resulting brown oil was purified by FlashMaster II. The crude material was dissolved in chloroform and added to the top of 2×100 g silica SPE cartridges that were subsequently eluted with 0-100% ethyl acetate:cyclohexane over 60 min. The product-containing fractions were combined and the solvent was removed in vacuo. The residue was dried on a high vacuum line to give the title product, 371 mg as a cream solid.

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customwas placed on a high vacuum line overnight
  4. customThe resulting brown oil was purified by FlashMaster II
  5. dissolutionThe crude material was dissolved in chloroform
  6. additionadded to the top of 2×100 g silica SPE cartridges that
  7. washwere subsequently eluted with 0-100% ethyl acetate
  8. customthe solvent was removed in vacuo
  9. customThe residue was dried on a high vacuum line

Sources & evidence

ORD record
ord-a0eaf770d21649d39453c22b2e3ebae1
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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