Toluene → HCID 78046451, compound

HRID 1055076Notes

Reaction equation

HRID 1055076 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:30]C=O)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:44][C:45]([O:47][CH3:48])=[O:46])C=CC=CC=1.[C:61]1(C)C=CC=CC=1>>[F:1][C:2]1[C:3]([NH:28][CH:29]([C:33]([CH3:36])([CH3:34])[CH3:35])[CH2:30][CH:61]=[CH:44][C:45]([O:47][CH3:48])=[O:46])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=3)(=[O:19])=[O:20])[CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86714755HCID 86714755, compound2×

Product 1

HCID 78046451HCID 78046451, compound

Procedure

To a solution of 3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-4,4-dimethylpentanal, 83a, (0.295 g, 0.574 mmol) in toluene (5.9 mL) was added methyl 2-(triphenylphosphoranylidene)acetate (0.300 g, 0.862 mmol). The mixture was stirred overnight at room temperature and then purified directly on silica gel (EtOAc/Hexanes) to afford 278 mg of the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.54 minutes (M+H) 584.12.

Workup

  1. custompurified directly on silica gel (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-68d134c9de6c46c29827251f40001c7a
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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