1,4-Dioxane → HCID 67456423, compound

HRID 1944280Notes

Reaction equation

HRID 1944280 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.C([Sn](CCCC)(CCCC)[C:37]1[O:38][CH:39]=[CH:40][N:41]=1)CCC.O1CCOCC1>C(OCC)(=O)C.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>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:37]3[O:38][CH:39]=[CH:40][N:41]=3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 66717642HCID 66717642, compound

Product 1

HCID 67456423HCID 67456423, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [3-(4-bromobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.36 g), 2-tributylstannanyloxazole (0.46 mL), tetrakis(triphenylphosphine)palladium(0) (0.084 g) and 1,4-dioxane (3.0 mL) was heated at 100° C. for 3 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound as a yellow gum (1.1 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ebd2a5632b4e475db45721a85be56c9e
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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