Potassium tert-butoxide → HCID 178435741, compound

HRID 2283505Notes

Reaction equation

HRID 2283505 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=2)[N:11]=[C:10]([C:25]2[CH:26]=[N:27][C:28]([C:31]([C@H:33]3[CH2:38][CH2:37][C@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:35][CH2:34]3)=O)=[CH:29][CH:30]=2)[CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C(OCC)(=O)C.O>[CH3:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=[CH:17][N:16]=2)[N:11]=[C:10]([C:25]2[CH:26]=[N:27][C:28]([C:31]([C@H:33]3[CH2:34][CH2:35][C@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:37][CH2:38]3)=[CH2:1])=[CH:29][CH:30]=2)[CH:9]=1

Participants

7

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178501135HCID 178501135, compound

Product 1

HCID 178435741HCID 178435741, compound

Reagents, catalysts & solvents 4

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a flask was added methyltriphenylphosphonium bromide (444 mg, 1.24 mmol) and THF (3.1 mL). The mixture was cooled to 0° C., and potassium tert-butoxide (1.0 M in THF, 1.39 mL, 1.39 mmol) was added. The mixture was stirred at 0° C. for 30 minutes. A solution of methyl trans-4-[(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)carbonyl]cyclohexanecarboxylate (310 mg, 0.622 mmol) in THF (2 mL) was added dropwise at 0° C., and the mixture was stirred at 0° C. for 30 minutes. The reaction was diluted with ethyl acetate and water, and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane (0-60%) to afford methyl trans-4-[1-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)ethenyl]cyclohexanecarboxylate as a white solid. MS ESI calcd. for C27H28F3N4O2 [M+H]+ 497. found 497.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/hexane (0-60%)

Sources & evidence

ORD record
ord-3425ef8399c045179e400a497308ef59
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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