Lithium Chloride → HCID 68312958, compound

HRID 1530725Notes

Reaction equation

HRID 1530725 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[C:18]([CH3:24])[N:17]=2)=[CH:10]3)=[CH:4][C:3]=1[O:25][CH3:26].C([Sn](CCCC)(CCCC)[C:32]([O:34][CH2:35][CH3:36])=[CH2:33])CCC.[Li+].[Cl-].[F-].[K+]>C1COCC1.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>[CH2:35]([O:34][C:32]([C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[C:18]([CH3:24])[N:17]=2)=[CH:10]3)=[CH:4][C:3]=1[O:25][CH3:26])=[CH2:33])[CH3:36]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68313010HCID 68313010, compound

Product 1

HCID 68312958HCID 68312958, compoundYield 130.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 13-bromo-12-methoxy-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen (1.55 g, 3.73 mmol), tributyl(1-ethoxyvinyl)stannane (1.35 g, 3.74 mmol), LiCl (472 mg, 11.2 mmol), and Pd(PPh3)4 (130 mg, 0.120 mmol) in THF (30 mL) in a sealed tube was stirred at 80° C. for 16 hrs under N2 atmosphere. After cooling to room temperature, aq. KF (2.0 M, 50.0 mL) was added. The resulting mixture was stirred at room temperature for 1 h and then filtered. The filtrate was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine and dried over MgSO4. Removal of the solvent gave the desired product (2.0 g) as pale yellow oil. LCMS m/z [M+H]+ 410.3

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe resulting mixture was stirred at room temperature for 1 h
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with ethyl acetate (5×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-f430deccf4a9401cbcb0fa309ffc7f09
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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