2-(Tributylstannyl)pyridine → HCID 86710431, compound

HRID 1398454Notes

Reaction equation

HRID 1398454 reaction equation
Br[C:2]1[C:18]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[N:10][C:9]=3[CH3:14].C([Sn](CCCC)(CCCC)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)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>[CH3:14][C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[C:7](=[O:15])[N:6]([CH3:16])[C:5]1[CH:17]=[C:18]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:22][CH:23]([CH3:25])[CH3:24])[C:2]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[CH:3][C:4]2=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 86710370HCID 86710370, compound

Product 1

HCID 86710431HCID 86710431, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-tert-butyl (1-((9-bromo-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (100 mg, 0.193 mmol) in 1,4-dioxane (2 mL) was added 2-(tributylstannyl)pyridine (85 mg, 0.231 mmol) and Pd(PPh3)4 (11.14 mg, 9.64 μmol). The reaction mixture was degassed for 30 min and heated to 120° C. for 1 h in a microwave. The reaction mixture was cooled and diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (3% methanol in chloroform) to afford (S)-tert-butyl (1-((4,6-dimethyl-5-oxo-9-(pyridin-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.120 mmol, 62% yield) as a pale yellow solid which was carried on without further purification LC/MS (ESI) m/e 517.7 [(M+H)+, calcd for C30H37N4O4 517.3]; LC/MS retention time (method E): tR=1.19 min.

Workup

  1. customThe reaction mixture was degassed for 30 min
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with water (10 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography (3% methanol in chloroform)

Sources & evidence

ORD record
ord-93ec3b808dfb490fa8a28e55fe6ef0fe
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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