Stannane, tributyl(1-ethoxyethenyl)- → HCID 59128943, compound

HRID 2390514Notes

Reaction equation

HRID 2390514 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]2[C:9]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:25]([F:28])([F:27])[F:26].C([Sn](CCCC)(CCCC)[C:34]([O:36][CH2:37][CH3:38])=[CH2:35])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>[C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:9]1[C:8]([NH:7][C:5]2[S:6][C:2]([C:34]([O:36][CH2:37][CH3:38])=[CH2:35])=[C:3]([C:25]([F:28])([F:27])[F:26])[N:4]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 59128919HCID 59128919, compound

Product 1

HCID 59128943HCID 59128943, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(5-bromo-4-(trifluoromethyl)thiazol-2-yl)-2-(2-tert-butylphenoxy)pyridin-3-amine (Example 323a, 1.3 g, 2.75 mmol) in dioxane (30 mL) was added tributyl(1-ethoxyvinyl)tin (1.1 mL, 3.3 mmol) was degassed and Pd(PPh3)4 (160 mg, 0.14 mmol) was added. The mixture was degassed and heated at 100° C. overnight. The mixture was concentrated on vacuum, dissolved in EtOAc and treated with saturated KF solution. The solid was removed by filtering through a pad of Celite®. The filtrate was extracted with EtOAc. The organic layers were combined, washed with bring, dried over magnesium sulfate and concentrated to give crude Example A154a (1.12 g) as a brown oil.

Workup

  1. customwas degassed
  2. customThe mixture was degassed
  3. concentrationThe mixture was concentrated on vacuum
  4. dissolutiondissolved in EtOAc
  5. additiontreated with saturated KF solution
  6. customThe solid was removed
  7. filtrationby filtering through a pad of Celite®
  8. extractionThe filtrate was extracted with EtOAc
  9. washwashed
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. customto give crude Example A154a (1.12 g) as a brown oil

Sources & evidence

ORD record
ord-bb2a0fa642674f4ab3d7e0dcc6d302de
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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