Cesium carbonate → 2-((4-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenoxy)methyl)quinoline

HRID 33937Notes

Reaction equation

HRID 33937 reaction equation
CN1C([C:7]2[CH:24]=[CH:23][C:10]([O:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)=C(C2C=CN=CC=2)N=N1.[N:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH:41]=[CH:40][N:39]=[C:38]2C2C=CC(O)=CC=2)=[CH:33][CH:32]=1.Cl.ClCC1C=CC2C(=CC=CC=2)N=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[N:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH:41]=[CH:40][N:39]=[C:38]2[C:7]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:23][CH:24]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 115384252-((4-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenoxy)methyl)quinolineHCID 1363758214-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenol

Product 1

HCID 116823322-((4-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenoxy)methyl)quinolineYield 84%

Procedure

According to the procedure for preparation of 2-((4-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenoxy)methyl)quinoline, 4-(1-(pyridin-4-yl)-1H-imidazol-2-yl)phenol (90 mg), 2-(chloromethyl)quinoline hydrochloride (81 mg) and cesium carbonate (495 mg) gave 120 mg as an off-white solid (84%). 1H NMR (CDCl3, 400 mHz) δ 8.59 (m, 2H), 8.16 (d, 1H, J =8.3 Hz), 8.04 (d, 1H, J=8.3 Hz), 7.79 (d, 1H, J=7.9 Hz), 7.70 (ddd, 1H), 7.60 (d, 1H, J=8.3 Hz), 7.52 (ddd, 1H), 7.28 (m, 2H), 7.22 (d, 1H, J=1 Hz), 7.15 (d, 1H, J=1 Hz), 7.11 (m, 2H), 6.94 (m, 2H), 5.34 (s, 2H). HPLC-MS (system 1) 4.53 min, m/e 379 (MH+).

Sources & evidence

ORD record
ord-66a0716e77db42c388b9130218c1716e
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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