4-Chlorophenol → HCID 67046320, compound

HRID 606012Notes

Reaction equation

HRID 606012 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=4)=[CH:11][N:10]3[CH:23]=2)=[CH:3][CH:2]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:22][CH2:21][C:17]2[CH:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]4[N:10]([CH:23]=[C:7]([C:4]5[CH:3]=[CH:2][C:1]([CH3:24])=[CH:6][CH:5]=5)[N:8]=4)[CH:11]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 24856033HCID 24856033, compound

Product 1

HCID 67046320HCID 67046320, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg of [3-(2-p-tolylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol (Example 3) are dissolved in 20 ml of dry tetrahydrofuran, 123 mg of p-chlorophenol, 193 mg of tributylphosphine and 210 mg of 1,1′-azodicarbonyldipiperidine are added thereto and the mixture is left to stir at ambient temperature for 16 h. The solvent is evaporated off under reduced pressure. The residue is taken up with 10 ml of ethyl acetate, the precipitate is removed, the filtrate is concentrated and the residue is purified by chromatography. The solid obtained is taken up with petroleum ether and the precipitate is recovered by filtration and dried under reduced pressure. 52 mg of compound are obtained. Mp=182-184° C. 1H NMR (DMSO-d6, δ in ppm): 2.32 (s, 3H); 5.17 (s, 2H); 7.06 (d, J=7 Hz, 2H); 7.23 (d, J=7.2 Hz, 2H); 7.32 (d, J=7.3 Hz, 2H); from 7.40 to 7.80 (m, 6H); 7.84 (m, J=7.8 Hz, 2H); 8.32 (s, 1H); 8.86 (m, 1H). M+H=425.

Workup

  1. waitthe mixture is left
  2. customThe solvent is evaporated off under reduced pressure
  3. customthe precipitate is removed
  4. concentrationthe filtrate is concentrated
  5. customthe residue is purified by chromatography
  6. customThe solid obtained
  7. filtrationthe precipitate is recovered by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-798bfb3da1c14d7ba763c2c515d0c9e8
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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