Triphenylarsine → HCID 86686127, compound

HRID 869151Notes

Reaction equation

HRID 869151 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C[Sn](C)C.C[Sn](C)C.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:38]1[N:43]=[N:42][C:41]([N:44]([CH2:52][C:53]([C:56]2[CH:61]=[CH:60][C:59]([F:62])=[CH:58][CH:57]=2)([CH3:55])[CH3:54])[C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:40][CH:39]=1>[F-].[K+].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.CN(C=O)C.O1CCOCC1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:38]2[N:43]=[N:42][C:41]([N:44]([CH2:52][C:53]([C:56]3[CH:57]=[CH:58][C:59]([F:62])=[CH:60][CH:61]=3)([CH3:54])[CH3:55])[C:45](=[O:51])[O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[CH:40][CH:39]=2)=[N:3][CH:4]=1)#[N:9]

Participants

9

Reactant 4

HCID 11773TriphenylarsineHCID 50057186-Bromopyridine-3-carbonitrileHCID 6327618HexamethylditinHCID 86686128HCID 86686128, compound

Product 1

HCID 86686127HCID 86686127, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 dram vial was added 2-bromo-5-cyanopyridine (182 mg, 1.0 mmol, 1.0 equiv), hexamethylditin (639 mg, 1.1 mmol, 1.1 equiv), Cl2Pd(Ph3P)2 (91 mg, 0.13 mmol, 0.13 equiv), triphenylarsine (34 mg, 0.11 mmol, 0.11 equiv), and dioxane (7 mL). The reaction mixture was stirred and heated to 80° C. for 12 h. The reaction was then concentrated, followed by the addition of tert-butyl 6-bromopyridazin-3-yl(2-(4-fluorophenyl)-2-methylpropyl)carbamate (423 mg, 1.0 mmol, 1.0 equiv), Pd(Ph3P)4 (172 mg, 0.15 mmol, 0.15 equiv), and DMF (3.3 mL). The reaction was stirred and heated to 100° C. for 3 h. After cooling to room temperature, the reaction was diluted with aqueous potassium fluoride (5 mL), extracted with ethyl acetate (20 mL) and washed with brine (20 mL). The organic layer was then dried (Na2SO4), filtered, and concentrated to give crude tert-butyl 6-(5-cyanopyridin-2-yl)pyridazin-3-yl(2-(4-fluorophenyl)-2-methylpropyl)carbamate.

Workup

  1. concentrationThe reaction was then concentrated
  2. stirringThe reaction was stirred
  3. temperatureheated to 100° C. for 3 h
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with ethyl acetate (20 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialThe organic layer was then dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8d7815b732c442bca9dee9a9716380c1
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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