1,4-Dioxane → HCID 56644360, compound

HRID 512027Notes

Reaction equation

HRID 512027 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[C:11]([Cl:18])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:21][S:22]([NH2:25])(=[O:24])=[O:23].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.N12CCCN=C1CCCCC2.[O:55]1CCOC[CH2:56]1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[Cl:18][C:11]1[C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:8]([O:7][CH2:6][C:5]2[CH:19]=[CH:20][C:2]([C:56]([NH:25][S:22]([CH3:21])(=[O:24])=[O:23])=[O:55])=[CH:3][CH:4]=2)=[N:9][CH:10]=1

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66667735HCID 66667735, compound

Product 1

HCID 56644360HCID 56644360, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
150 °C

Procedure

A solution of 2-(4-bromobenzyloxy)-5-chloro-4-(trifluoromethyl)pyridine (Preparation 106, 0.2 g, 0.54 mmol), methanesulfonamide (0.13 g, 0.162 mmol), tri-tert-butylphosphonium tetrafluoroborate (26 mg, 0.027 mmol), Herrmann's palladacycle (26 mg, 0.027 mmol) and molybdenehexacarbonyl (142 mg, 0.54 mmol) was stirred in dioxane (2 mL). 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.25 mL, 0.162 mmol) was added in one portion, and the vial was sealed and heated in a microwave for 15 minutes at 150° C. The solvent was evaporated in vacuo. The residue was extracted with dichloromethane (30 mL) and washed with water (10 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting solid was purified on a 10 g silica cartridge (eluent:dichloromethane, followed by 3% methanol in dichloromethane) to afford the title compound (55 mg, 25%) as a beige solid.

Workup

  1. customthe vial was sealed
  2. customThe solvent was evaporated in vacuo
  3. extractionThe residue was extracted with dichloromethane (30 mL)
  4. washwashed with water (10 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting solid was purified on a 10 g silica cartridge (eluent:dichloromethane, followed by 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ec2f4227ee974e61b3ce9a71ec467fab
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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