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

HRID 1157767Notes

Reaction equation

HRID 1157767 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 16 h 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, 1H) 8.35 (s, 1H) 8.31 (d, J=2.75 Hz, 1H) 7.52-7.62 (m, 5H) 3.81-3.85 (m, 2H) 3.61-3.65 (m, 2H) 3.39-3.43 (m, 2H) 3.31-3.35 (m, 2H) 2.80-2.83 (m, 3H).

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 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-396744af6f1e47c4801cd42c55325af5
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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