Stannane, tributyl(1-ethoxyethenyl)- → HCID 49770160, compound

HRID 1157301Notes

Reaction equation

HRID 1157301 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([F:32])=[C:6]2[C:10]([C:11](=[O:31])[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12.C([Sn](CCCC)(CCCC)[C:38]([O:40]CC)=[CH2:39])CCC>O1CCOCC1.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:38]([C:2]1[N:3]=[CH:4][C:5]([F:32])=[C:6]2[C:10]([C:11](=[O:31])[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12)(=[O:40])[CH3:39]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 595113051-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione

Product 1

HCID 49770160HCID 49770160, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a sealable flask containing 1-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.10 g, 0.20 mmol) in 1,4-dioxane (5 mL) was added tributyl(1-ethoxyvinyl)tin (0.079 g, 0.22 mmol) followed by Pd(PPh3)4 (0.07 g, 0.06 mmol). The mixture was flushed with N2, and the tube was sealed and heated to 100° C. After 16h of heating, the mixture was cooled to rt, and the solvent was removed in vacuo. The residue was dissolved in DMF and was filtered through a pad of celite to remove any remaining solids. The DMF solution was purified by prep HPLC to give the title compound as an off-white solid (0.025 g). LCMS: m/e 463.38 (M+H)+, ret time 1.88 min (method 2). 1H NMR (500 MHz, CDCl3) δ ppm 11.02 (s, 1 H) 8.35 (s, 1 H) 8.31 (d, J=2.75 Hz, 1 H) 7.52-7.62 (m, 5 H) 3.81-3.85 (m, 2 H) 3.61-3.65 (m, 2 H) 3.39-3.43 (m, 2 H) 3.31-3.35 (m, 2 H) 2.80-2.83 (m, 3 H).

Workup

  1. customThe mixture was flushed with N2
  2. customthe tube was sealed
  3. temperatureAfter 16h of heating
  4. temperaturethe mixture was cooled to rt
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in DMF
  7. filtrationwas filtered through a pad of celite
  8. customto remove any remaining solids
  9. customThe DMF solution was purified by prep HPLC

Sources & evidence

ORD record
ord-73606a29a19a41c4812767131b39f94b
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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