Triethylamine → 1-[3-(2-Methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidine

HRID 601502Notes

Reaction equation

HRID 601502 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH2:13]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:14]#[CH:15].CCN(CC)CC>C(#N)C.CCOC(C)=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:15]#[C:14][CH2:13][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 2301031-Iodo-2-methoxy-4-nitrobenzeneHCID 2996161-(Prop-2-yn-1-yl)pyrrolidine

Product 1

HCID 574214681-[3-(2-Methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidineYield 51%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 1-iodo-2-methoxy-4-nitro-benzene (618 mg, 2.21 mmol) in acetonitrile (10 mL) and treat sequentially with 1-prop-2-ynyl-pyrrolidine (352 mg, 3.22 mmol), Et3N (2 mL), CuI (77 mg, 0.404 mmol) and Pd(PPh3)4 (360 mg, 0.311 mmol). Stir the mixture at room temperature for 3 h, then dilute with EtOAc (50 mL) and wash with saturated NaHCO3 (30 mL). Dry, filter and concentrate the organic solution. Purify the crude material by flash chromatography, using a linear gradient of 50% EtOAc/hexanes to 100% EtOAc, to give the title compound as an orange oil (292 mg, 51%). MS (ES+) 261.1 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.77 (dd, 1H, J=8.3, 2.2 Hz), 7.70 (d, 1H, J=2.2 Hz), 7.50 (d, 1H, J=8.3 Hz), 3.95 (s, 3H), 3.72 (s, 2H), 2.75-2.70 (m, 4H), 1.87-1.83 (m, 4H).

Workup

  1. washwash with saturated NaHCO3 (30 mL)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic solution
  5. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-1452c8a1f1b047f386368532a6843971
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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