Sodium Hydroxide → 8-((1H-imidazol-5-yl)(pyridin-2-yl)methyl)quinoline

HRID 390363Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[N:41]=[CH:40][CH:39]=[CH:38]2)([C:9]1[N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:12]=[N:11][CH:10]=1)O.[OH-].[Na+]>I.CC(O)C.C(Cl)(Cl)Cl>[NH:13]1[C:9]([CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[C:37]3[C:42]=2[N:41]=[CH:40][CH:39]=[CH:38]3)=[CH:10][N:11]=[CH:12]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of pyridin-2-yl(quinolin-8-yl)(1-trityl-1H-imidazol-5-yl)methanol (Intermediate 14) (385 mg, 0.70 mmol) in 57% aqueous HI (10 mL) and iPrOH (2 mL) was added red phosphorus (219 mg, 7.0 mmol) in a resealable tube was heated at 160° C. for 16 h. The mixture was then cooled to room temperature and poured into ice-water, which was then basified with NaOH and diluted with CHCl3. The residue was isolated in a typical aqueous workup using CHCl3 and purified by MPLC with 5 to 15% MeOH:CH2Cl2 to give 8-((1H-imidazol-5-yl)(pyridin-2-yl)methyl)quinoline, (658) as a solid, 236 mg (61% in two steps). 1HNMR (CD3OD, 300 MHz) δ 8.82 (dd, J=1.8, 4.5 Hz, 1H), 8.43 (dd, J=1.8, 5.7 Hz, 1H), 8.28 (dd, J=1.8, 8.4 Hz, 1H), 7.83 (dd, J=4.0, 7.8 Hz, 1H), 7.73-7.70 (m, 2H), 7.68-7.43 (m, 3H), 7.25-7.21 (m, 2H), 7.03 (s, 1H), 6.52 (s, 1H).

Workup

temperatureThe mixture was then cooled to room temperature
customThe residue was isolated in a typical aqueous workup
custompurified by MPLC with 5 to 15% MeOH

Sources & evidence

ORD record: ord-f71d141937dc49a78ba4fe53b2332823
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383646B2

Reaction notes

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