2-Fluoro-4-iodoaniline → HCID 18428007, compound

HRID 1279382Notes

Reaction equation

HRID 1279382 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[CH:16])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[F:19][C:20]1[CH:26]=[C:25](I)[CH:24]=[CH:23][C:21]=1[NH2:22]>C(N)CCC.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>[NH2:22][C:21]1[CH:23]=[CH:24][C:25]([C:16]#[C:15][CH2:14][CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:26][C:20]=1[F:19]

Participants

5

Reactant 2

HCID 1856942-Fluoro-4-iodoanilineHCID 106828724-(4-Chlorobenzyl)-1-(3-butynyl)piperidine

Product 1

HCID 18428007HCID 18428007, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8007ButylamineSolvent

Procedure

To a solution of 4-(4-chlorobenzyl)-1-(but-3-yn-1-yl)piperidine (400 mg, 1.53 mmol) and 2-fluoro-4-iodoaniline (436 mg, 1.84 mmol) in 10 mL of butylamine is added 70 mg of Pd(PPh3)4. The resulting solution is allowed to reflux for 24 hr. The solvent is evaporated in vacuo and the residue is purified by flash chromatography giving the title product as a brown oil (100 mg, 18%): 1H NMR (CDCl3) 1.25 (m, 2 H), 1.46 (m, 1 H), 1.58 (m, 2 H), 1.97 (m, 2 H), 2.56 (m, 6 H), 2.88 (m, 2 H), 3.83 (bs, 2 H), 6.62 (m, 1 H), 6.80-7.24 (m, 6 H).

Workup

  1. temperatureto reflux for 24 hr
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-5f5bf0bfaf6d4aee835fc2c9f62b1f80
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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