2-(Tri-n-butylstannyl)oxazole → HCID 68472426, compound

HRID 387669Notes

Reaction equation

HRID 387669 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.C([Sn](CCCC)(CCCC)[C:29]1[O:30][CH:31]=[CH:32][N:33]=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>[O:30]1[CH:31]=[CH:32][N:33]=[C:29]1[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 68473018HCID 68473018, compound

Product 1

HCID 68472426HCID 68472426, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
145 °C

Procedure

Added to a solution of 0.8 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 8 cm3 of dioxane, under an argon atmosphere at a temperature close to 20° C. are 308 mg of tetrakis(triphenylphosphine)palladium and 3.2 g of 2-(tri-n-butylstannyl)oxazole. The reaction medium is heated at 145° C. in a microwave oven for 15 minutes, then left to return to a temperature close to 20° C. The reaction medium is concentrated to dryness under reduced pressure (5 kPa). The residue is taken up by 5 cm3 of dichloromethane and purified by flash chromatography over silica (column: 110 g; spherical silica of BP-SUP type particle size: 20-40 μm; eluent: 90% heptane/10% ethyl acetate then 100% ethyl acetate). After concentrating the fractions under reduced pressure, 320 mg of methyl 7-(2-oxazolyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained.

Workup

  1. customclose to 20° C.
  2. waitleft
  3. customclose to 20° C
  4. concentrationThe reaction medium is concentrated to dryness under reduced pressure (5 kPa)
  5. custompurified by flash chromatography over silica (column
  6. concentrationAfter concentrating the fractions under reduced pressure, 320 mg of methyl 7-(2-oxazolyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  7. customare obtained

Sources & evidence

ORD record
ord-825cc54a71404db496b6ee702e443704
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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