Lithium Chloride → HCID 68540418, compound

HRID 1992281Notes

Reaction equation

HRID 1992281 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@:9]2([CH3:19])[CH2:14][CH2:13][S:12][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:20][C:21]1[C:26]([Sn](CCCC)(CCCC)CCCC)=[N:25][CH:24]=[CH:23][N:22]=1.[Cl-].[Li+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C@:9]2([CH3:19])[CH2:14][CH2:13][S:12][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[N:10]2)=[CH:3][C:2]=1[C:26]1[C:21]([F:20])=[N:22][CH:23]=[CH:24][N:25]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 121306622-Fluoro-3-(tributylstannyl)pyrazineHCID 68539553HCID 68539553, compound

Product 1

HCID 68540418HCID 68540418, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

To solution of (S)-N-(4-(3-bromo-4-fluorophenyl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)acetamide (500 mg, 1.5 mmoles, 1 equiv), 2-fluoro-3-(tributylstannyl)pyrazine (1.7 g, 4.3 mmoles, 3.0 equiv) in toluene (15 mL) is added bis(triphenylphosphine)palladium(II) chloride (51 mg, 72 μmoles, 0.05 equiv) and lithium chloride (92 mg, 2.2 mmoles, 1.5 equiv). The reaction is irradiated in a laboratory-grade microwave to a temperature of 130° C. and held for 3 h. The solvent is removed under reduced pressure and the residue is purified by silica gel chromatography eluting with a linear gradient of hexane to hexane:ethyl acetate (1:1) ramp 20 min to give the title compound (31% yield): MS (m/z): 363 (M+1).

Workup

  1. customThe reaction is irradiated in a laboratory-grade microwave to a temperature of 130° C.
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is purified by silica gel chromatography
  4. washeluting with a linear gradient of hexane to hexane:ethyl acetate (1:1)
  5. waitramp 20 min

Sources & evidence

ORD record
ord-a30ae57a935a457ea972b563d951d122
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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