3-Methoxypropyne → HCID 22025687, compound

HRID 1835654Notes

Reaction equation

HRID 1835654 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10]([O:13][CH3:14])[C:11]#[CH:12]>C(OCC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([C:12]#[C:11][CH2:10][O:13][CH3:14])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 2

HCID 693933-MethoxypropyneHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 22025687HCID 22025687, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Fluoro-4-iodoaniline (2.00 g, 8.44 mmol), CuI (32 mg, 0.17 mmol), and (Ph3P)2PdCl2 (119 mg, 0.17 mmol) were weighed into a flask which was sealed and flushed with N2. A solution of methyl propargyl ether (0.65 g, 9.28 mmol) in TEA (8 mL) was added, then the entire mixture stirred 15 hours at room temperature. The reaction mixture was diluted with diethyl ether (100 mL), filtered through Celite®, then all solvents removed under reduced pressure. The resulting dark brown oil was purified by filtration through a plug of flash silica (10% EtOAc/hexanes as eluant) to afford 2-fluoro-4-(3-methoxy-1-propynyl)aniline as a pale orange oil which rapidly solidified to give a dark orange solid (1.38 g, 91%); 1H NMR [400 MHz, (CD3)2SO] δ 7.07 (dd, J=12.2, 1.8 Hz, 1 H), 6.98 (dd, J=8.2, 1.7 Hz, 1 H), 6.71 (dd, J=9.3, 8.4 Hz, 1 H), 5.56 (s, 2 H), 4.26 (s, 2 H), 3.29 (s, 3 H).

Workup

  1. customwhich was sealed
  2. customflushed with N2
  3. filtrationfiltered through Celite®
  4. customall solvents removed under reduced pressure
  5. filtrationThe resulting dark brown oil was purified by filtration through a plug of flash silica (10% EtOAc/hexanes as eluant)

Sources & evidence

ORD record
ord-ff08fe14e35f4c749488df063b0d2a95
Source dataset
uspto-grants-2004_08
Patent number
US06770778B2

Reaction notes

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