4-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine → 3-Fluoro-6-[2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 520591Notes

Reaction equation

HRID 520591 reaction equation
[F:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([Sn](C)(C)C)=[CH:6][C:5]=2[N:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1.Br[C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[N:32]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:33]([CH3:35])=[CH:34][C:27]=12>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>[F:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]4[N:32]([S:36]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)(=[O:37])=[O:38])[C:33]([CH3:35])=[CH:34][C:27]=34)=[CH:6][C:5]=2[N:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1

Participants

5

Reactant 2

HCID 497590984-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridineHCID 583564173-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

Product 1

HCID 666957483-Fluoro-6-[2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-(phenylsulfonyl)-1H-indazol-4-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-Fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (660 mg), Pd(PPh3)4 (168 mg) and 4-bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (613 mg) were weighed into a microwave vial and DMF (10 ml) was added. The mixture was heated to 120° C. overnight. The mixture was then cooled to RT and the solvent was removed in vacuo. The crude material was dried in a vacuum oven overnight. The resulting dark 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 80 min. The product-containing fractions were combined and the solvent removed in vacuo to give the title compound, 357 mg as a cream solid.

Workup

  1. additionwas added
  2. temperatureThe mixture was then cooled to RT
  3. customthe solvent was removed in vacuo
  4. dry with materialThe crude material was dried in a vacuum oven overnight
  5. customThe resulting dark brown oil was purified by FlashMaster II
  6. dissolutionThe crude material was dissolved in chloroform
  7. additionadded to the top of 2×100 g silica SPE cartridges that
  8. washwere subsequently eluted with 0-100% ethyl acetate
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6e823bc52e134c73a04b7afcfb2755ea
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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