HCID 59693914, compound → HCID 59511507, compound

HRID 1157782Notes

Reaction equation

HRID 1157782 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]2[C:10]([C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][NH:8][C:7]=12.C([Sn](CCCC)(CCCC)[C:24]1[CH:28]=[C:27]([C:29]([OH:34])([CH2:32][CH3:33])[CH2:30][CH3:31])[NH:26][N:25]=1)CCC>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.O1CCOCC1>[OH:34][C:29]([C:27]1[NH:26][N:25]=[C:24]([C:2]2[N:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]3[C:10]([C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][NH:8][C:7]=23)[CH:28]=1)([CH2:32][CH3:33])[CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 59693914HCID 59693914, compoundHCID 68693600HCID 68693600, compound

Product 1

HCID 59511507HCID 59511507, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

To a sealable flask containing methyl 2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (0.070 g, 0.262 mmol) and 3-(3-(tributylstannyl)-1H-pyrazol-5-yl)pentan-3-ol (0.116 g, 0.262 mmol) was added tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol). 1,4-Dioxane (5 ml) was added and the mixture was flushed with N2. The tube was sealed, and the mixture was heated to 115° C. After 16 h of heating, the mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was diluted with MeOH and was filtered through a pad of celite to remove any solids. The solution was concentrated again under reduced pressure and the residue was dissolved in DMF and was purified by prep HPLC to give the product, methyl 2-(7-(5-(3-hydroxypentan-3-yl)-1H-pyrazol-3-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (0.073 g, 0.189 mmol, 72.2% yield) as an off-white solid. LCMS: m/e 387.19 (M+H)+, ret time 1.075 min (method 3).

Workup

  1. customthe mixture was flushed with N2
  2. customThe tube was sealed
  3. temperatureAfter 16 h of heating
  4. temperaturethe mixture was cooled to rt
  5. customthe solvent was removed under reduced pressure
  6. additionThe residue was diluted with MeOH
  7. filtrationwas filtered through a pad of celite
  8. customto remove any solids
  9. concentrationThe solution was concentrated again under reduced pressure
  10. dissolutionthe residue was dissolved in DMF
  11. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-80035036de894d50843b43da8df4074a
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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