Tetrahydrofuran → HCID 71008816, compound

HRID 1616929Notes

Reaction equation

HRID 1616929 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1COCC1.C([Si](C(C)C)(C(C)C)[S-])(C)C.[Li+].[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]2[C:52]3[CH:58]=[CH:57][C:56](I)=[CH:55][C:53]=3[O:54][C:48]=2[C:47]1([CH3:61])[CH3:60])=[O:45])([CH3:42])([CH3:41])[CH3:40]>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:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]2[C:52]3[CH:58]=[CH:57][C:56]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])=[CH:55][C:53]=3[O:54][C:48]=2[C:47]1([CH3:61])[CH3:60])=[O:45])([CH3:42])([CH3:40])[CH3:41]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 3435097Tris(propan-2-yl)silanethiolHCID 67324040HCID 67324040, compoundHCID 86672977HCID 86672977, compound

Product 1

HCID 71008816HCID 71008816, compoundYield 130.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

Anhydrous dioxane was bubbled with Argon for 1 h before being used. Triisopropylsilanethiol (4.00 mL, 18.6 mmol) was dissolved into anhydrous 1,4-dioxane (15 mL) and a solution of lithium hexamethyldisilazide in THF (1.0 M 17.7 mL, 17.7 mmol) was added slowly. The reaction was stirred for 2.5 h. A portion of the lithium triisopropylsilanethiolate solution (15.4 mL, 7.70 mmol) was added to a suspension of 7-iodo-1,1-dimethyl-3,4-dihydro-1H-benzo[4,5]furo[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (3.00 g, 7.02 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.81 g, 0.70 mmol) in 1,4-dioxane (10 mL) under argon. The reaction mixture was stirred at 60° C. for 2 h and the solvent was evaporated. The residue was triturated with anhydrous hexane, filtered through a plug of Celite and the filtrate was concentrated down to yield 4.48 g of 1,1-dimethyl-7-triisopropylsilanylsulfanyl-3,4-dihydro-1H-benzo[4,5]furo[2,3-c]pyridine-2-carboxylic acid tert-butyl ester. This product was used in the next step without further purification. MS m/z 490 [M+H]+

Workup

  1. customAnhydrous dioxane was bubbled with Argon for 1 h
  2. stirringThe reaction mixture was stirred at 60° C. for 2 h
  3. customthe solvent was evaporated
  4. customThe residue was triturated with anhydrous hexane
  5. filtrationfiltered through a plug of Celite
  6. concentrationthe filtrate was concentrated down

Sources & evidence

ORD record
ord-22510fe33c7748b7a1ec5127b381910f
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…