Triphenylphosphine → N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

HRID 392445Notes

Reaction equation

HRID 392445 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.O[CH2:23][C:24]1[CH:25]=[C:26]([N:30]([CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=1>>[Br:20][CH2:23][C:24]1[CH:25]=[C:26]([N:30]([CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 23521701n-(3-Hydroxymethylphenyl)-n-(ethylsulfonyl)pyrid-3-ylmethylamine

Product 1

HCID 23521695N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

Procedure

Resin-supported triphenylphosphine (1.6 g, 3 mmol per gram resin) was dispersed on dichloromethane. At 0° C., bromine (0.850 g, 5.3 mmol) solution was added dropwise to the resin. And the mixture was stirred for 15 min, followed by dropping a solution of N-(3-hydroxymethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.930 g, 3 mmol). After 1 h, the resin was filtered and washed with CHCl3. Evaporation afforded the title compound. 1H NMR:, 8.81 (s,1H), 8.68 (d,1H, J=5.4 Hz), 8.47 (d,1H,J=8.3 Hz), 7.91 (m,1H), 7.26-7.39 (m,1H), 5.16 (s,2H), 4.40 (s,2H), 3.12 (q,2H,J=7.3 Hz), 1.40 (t,3H,J=7.3 Hz). MS calcd. 370.0; MS (M+1) 371.1.

Workup

  1. waitAfter 1 h
  2. filtrationthe resin was filtered
  3. washwashed with CHCl3
  4. customEvaporation

Sources & evidence

ORD record
ord-76164c77a3ff46faa195bdbc2ae96f07
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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