2-Bromo-5-methylpyridine → HCID 58333407, compound

HRID 2066890Notes

Reaction equation

HRID 2066890 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC([O-])(C)C.[Na+].[NH:49]1[CH2:54][CH2:53][CH:52]([O:55][N:56]=[C:57]2[CH2:62][CH2:61][N:60]([C:63]3[CH:68]=[CH:67][C:66]([S:69]([CH3:72])(=[O:71])=[O:70])=[CH:65][C:64]=3[F:73])[CH2:59][CH2:58]2)[CH2:51][CH2:50]1.Br[C:75]1[CH:80]=[CH:79][C:78]([CH3:81])=[CH:77][N:76]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:81][C:78]1[CH:79]=[CH:80][C:75]([N:49]2[CH2:54][CH2:53][CH:52]([O:55][N:56]=[C:57]3[CH2:62][CH2:61][N:60]([C:63]4[CH:68]=[CH:67][C:66]([S:69]([CH3:72])(=[O:70])=[O:71])=[CH:65][C:64]=4[F:73])[CH2:59][CH2:58]3)[CH2:51][CH2:50]2)=[N:76][CH:77]=1

Participants

7

Reactant 4

HCID 5642162-Bromo-5-methylpyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 58333407HCID 58333407, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Pd2 dba3 (1.5 mg, 0.0016 mmol), Xantphos (2.8 mg, 0.0048 mmol), NaOtBu (11.5 mg, 0.12 mmol), 63a (29.5 mg, 0.08 mmol) and 2-bromo-5-methyl-pyridine (27.5 mg, 0.16 mmol) were combined. Toluene (0.3 mL) was added and the mixture was flushed with nitrogen, sealed and heated at 100° C. overnight. The solvent was removed and the crude mixture was purified on preparative HPLC to give 67-1: LC-MS 461.2 (MH+).

Workup

  1. customthe mixture was flushed with nitrogen
  2. customsealed
  3. customThe solvent was removed
  4. customthe crude mixture was purified on preparative HPLC
  5. customto give 67-1

Sources & evidence

ORD record
ord-13654952b0aa478d93c5f3f733dc183a
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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