Dichloromethane → 4-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenol

HRID 33935Notes

Reaction equation

HRID 33935 reaction equation
CN1C(C2C=CC(O)=CC=2)=C(C2C=CN=CC=2)N=N1.ClCCl.C[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:32]([C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[CH:33]=[CH:34][N:35]=2)=[CH:27][CH:26]=1.B(Br)(Br)Br>CC(O)C>[N:39]1[CH:38]=[CH:37][C:36]([N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[C:28]2[CH:29]=[CH:30][C:25]([OH:24])=[CH:26][CH:27]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 571501814-(2-(4-methoxyphenyl)-1H-imidazol-1-yl)pyridineHCID 1363758384-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenol

Product 1

HCID 1363758214-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenolYield 75.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

According to the procedure for preparation of 4-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenol, except that 4:1 dichloromethane:2-propanol was used in place of ethyl acetate to extract the product, 4-(2-(4-methoxyphenyl)-1H-imidazol-1-yl)pyridine (125 mg, 0.5 mmol) was treated with 1.25 mmol of boron tribromide to give 90 mg of a colorless solid. 1H NMR (CDCl3, 400 mHz) δ 8.52 (d, 2H, J=6 Hz), 7.14 (m, 2H), 7.11-7.08 (m, 4H), 6.79 (m, 2H), 2.94 (br, 1 H).

Sources & evidence

ORD record
ord-41285d6e3aca4d27bc7793222fba6792
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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