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Cyclopentylamine → Ethyl 4-cyano-3-(cyclopentylamino)benzoate

HRID 906143
Notes
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Reaction equation

HRID 906143 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[N:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].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.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:63]1([NH2:68])[CH2:67][CH2:66][CH2:65][CH2:64]1>O1CCOCC1.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]>[C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[NH:68][CH:63]1[CH2:67][CH2:66][CH2:65][CH2:64]1)#[N:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 2906CyclopentylamineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 18374323Ethyl 3-bromo-4-cyanobenzoate

Product 1

HCID 67404316Ethyl 4-cyano-3-(cyclopentylamino)benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), XANTPHOS (228 mg, 0.39 mmol), cesium carbonate (1.282 g, 3.94 mmol), cyclopentylamine (233 mg, 2.75 mmol), and tris(dibenzylideneacetone)dipalladium (180 mg, 0.20 mmol) in dioxane (5 mL) was stirred at 100° C. for 17 h. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL), the organic layer washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes:ethyl acetate 9:1) afforded ethyl 4-cyano-3-(cyclopentylamino)benzoate (366 mg, 72% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): 7.43 (m, 2H), 7.35 (m, 1H), 7.27 (m, 1H), 4.62 (d, 1H), 4.38 (q, 2H), 3.93 (m, 1H), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.53 (m, 2H), 1.39 (t, 3H). MS (EI) for C15H18N2O2: 259 (MH+).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL)
  2. washthe organic layer washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3eb8b5c8fab49148cfdb80524cfa6a5
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012956B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes