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3-(Tributylstannyl)cyclohex-2-enone → HCID 57489644, compound

HRID 2044095
Notes
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Reaction equation

HRID 2044095 reaction equation
Cl[C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:30]1[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH:31]=1)CCC>CN(C=O)C.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:11][C:10]1[C:2]([C:30]2[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH:31]=2)=[N:3][C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 137768013-(Tributylstannyl)cyclohex-2-enoneHCID 574896456-Chloro-5-fluoro-2-(4-morpholinophenylamino)nicotinamide

Product 1

HCID 57489644HCID 57489644, compoundYield 23.5%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-chloro-5-fluoro-2-(4-morpholinophenylamino)nicotinamide (80 mg, 0.228 mmol), 3-(tributylstannyl)cyclohex-2-enone (105 mg, 0.274 mmol) (synthesized according to literature procedure: Tet. Lett., 31:1837-1840 (1990)), and dichloro bis(triphenylphosphine)palladium (II) (16.05 mg, 0.023 mmol) in DMF (2 mL) was microwaved at 160° C. for 1 h. The reaction mixture was diluted with methylene chloride, washed with satd. NaHCO3, water, and concentrated. The residue was purified prep-HPLC. The product containing fractions were collected, basified with 1N NaOH, and extracted with methylene chloride twice. The combined organic fractions were washed with water, concentrated, and further purified by MPLC (ISCO, 5% ammonia/methanol/methylene chloride, 40 g silica gel column) to give 22 mg brown solid. LC-MS: (M+H)+=411.25. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.76-10.84 (1H, m), 8.28-8.39 (1H, m), 8.13-8.21 (1H, m), 7.83-7.91 (1H, m), 7.45-7.53 (2H, m), 6.88-6.96 (2H, m), 6.52-6.57 (1H, m), 3.67-3.77 (4H, m), 3.04 (4H, d, J=4.95 Hz), 2.76-2.85 (2H, m), 2.39-2.46 (2H, m), 2.01-2.09 (2H, m).

Workup

  1. washwashed with satd
  2. concentrationNaHCO3, water, and concentrated
  3. customThe residue was purified prep-HPLC
  4. additionThe product containing fractions
  5. customwere collected
  6. extractionextracted with methylene chloride twice
  7. washThe combined organic fractions were washed with water
  8. concentrationconcentrated
  9. customfurther purified by MPLC (ISCO, 5% ammonia/methanol/methylene chloride, 40 g silica gel column)

Sources & evidence

ORD record
ord-f15e82ba1ddc45239002fc49124fd2fb
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08586751B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes