1,4-Dioxane → HCID 56644359, compound

HRID 512028Notes

Reaction equation

HRID 512028 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:17][S:18]([NH2:21])(=[O:20])=[O:19].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.N12CCCN=C1CCCCC2.[O:51]1CCOC[CH2:52]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:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([C:52]([NH:21][S:18]([CH3:17])(=[O:20])=[O:19])=[O:51])=[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 66667687HCID 66667687, compound

Product 1

HCID 56644359HCID 56644359, compoundYield 37%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
140 °C

Procedure

A solution of 2-(4-bromobenzyloxy)-5-chloropyridine (Preparation 107, 0.12 g, 0.40 mmol), methanesulfonamide (0.10 g, 0.12 mmol), tri-tert-butylphosphonium tetrafluoroborate (12 mg, 0.04 mmol), Herrmann's palladacycle (18 mg, 0.02 mmol) and molybdenehexacarbonyl (105 mg, 0.40 mmol) was stirred in dioxane (2 mL). 1,8-diazabicyclo[5.4.0]undec-7-ene (0.18 mL, 0.12 mmol) was added in one portion, then the vial was sealed and heated in a microwave for 15 minutes at 140° 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. The resulting solid was purified on a 10 g silica cartridge (eluent:dichloromethane, followed by 3% methanol in dichloromethane) to afford the title compound (51 mg, 37%) as a beige solid. This was purified further by preparative HPLC.

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
  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-9f1e221d4ed74e6aa1a70986a59152ae
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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