Triethylamine → HCID 23003955, compound

HRID 396725Notes

Reaction equation

HRID 396725 reaction equation
[C:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](I)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O:19]1[CH2:24][CH2:23][CH:22]=[CH:21][C:20]1=[O:25].C(N(CC)CC)C>CN(C)C=O.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:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:22]3[CH2:23][CH2:24][O:19][C:20](=[O:25])[CH2:21]3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5206603393-45-1HCID 23003932HCID 23003932, compound

Product 1

HCID 23003955HCID 23003955, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1-boc-6-iodo-1,2,3,4-tetrahydroquinoline (2.0 g, Reference Example 12), 5,6-dihydro-pyran-2-one (1.1 g), tetrakis(triphenylphosphine)palladium(0) and triethylamine (2.2 g) in dimethylformamide (5 ml) was stirred at about 95° C. in a sealed vessel under an atmosphere of nitrogen overnight. The reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid, the layers separated, and the organic layer washed with sodium bicarbonate solution, then dried, and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:3,v/v) to give the title compound as a brown oil, 1.2 g.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  2. customthe layers separated
  3. washthe organic layer washed with sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:3,v/v)

Sources & evidence

ORD record
ord-0c5eb784e32f40dfbe85edcd0247a7cf
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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