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Diisopropylamine → N-methoxy-N-methyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-carboxamide

HRID 494829
Notes
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Reaction equation

HRID 494829 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1I.[CH2:15]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH3:24])[CH2:16][C:17]#[CH:18].CC1C=CC(P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C(NC(C)C)(C)C>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu](I)I>[CH3:11][O:10][N:8]([CH3:9])[C:6]([C:5]1[CH:12]=[CH:13][C:2]2[O:1][C:17]([CH2:16][CH2:15][N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[CH3:24])=[CH:18][C:3]=2[CH:4]=1)=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 13956Phosphine, tris(4-methylphenyl)-HCID 11367023(R)-1-(But-3-yn-1-yl)-2-methylpyrrolidineHCID 117712104-hydroxy-3-iodo-N-methoxy-N-methylbenzamide

Product 1

HCID 11438480N-methoxy-N-methyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-carboxamideYield 10.2%

Reagents, catalysts & solvents

3
HCID 83717Copper iodideCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

The product from Example 71D (11.6 g, 37.77 mmol) in acetonitrile (50 mL) was treated sequentially with a 0.12M solution of the product from Example 68B (378 mL, 45.33 mmol), Pd(OAc)2 (0.254 g, 1.13 mmol), tris(4-methylphenyl)phosphine (0.518 g, 1.699 mmol), and diisopropyl amine (39.7 mL, 283.3 mmol). After stirring at 25° C. for 10 minutes, the mixture was treated with copper iodide (2.158 g, 11.33 mmol) and heated at 50° C. in an inert atmosphere for 18 hours. The reaction mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel using 95% DCM, 9.9% MeOH, 0.1% NH4OH to provide the title compound (1.22 g, 10.2% yield). 1HNMR (300MHz, CD3OD) δ 1.18 (d, 3H, J=6.1 Hz), 1.47 (m, 1H), 1.78 (m, 2H), 1.91-2.34 (m, 2H), 2.50 (m, 2H) 3.06 (m, 2H), 3.26 (m, 2H), 3.38 (s, 3H), 3.59 (s, 3H), 6.63 (s, 1H), 7.51 (q, 2H), 7.84 (1H); MS (ESI) m/z 317.2 (M+H)+.

Workup

  1. temperatureheated at 50° C. in an inert atmosphere for 18 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified on silica gel using 95% DCM, 9.9% MeOH, 0.1% NH4OH

Sources & evidence

ORD record
ord-dc151b476a42447c9c038bff6c8daf99
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538138B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes