Methyl iodide → HCID 11211181, compound

HRID 2053458Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[NH:14][CH:15]=[N:16][CH:17]=1)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:24])[C:7](=[O:12])[C:6]([C:13]1[NH:14][CH:15]=[N:16][CH:17]=1)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A flask containing 6-bromo-3-(3H-imidazol-4-yl)-4-phenyl-1H-quinolin-2-one (23 mg, 0.063 mmol) (Example 134), K2CO3 (30 mg, 0.22 mmol), methyl iodide (4 μL, 0.063 mmol) and 0.1 mL of DMF was stirred at 25° C. for 3 hrs. The compound was purified by RP-HPLC, eluting with 30-70% CH3CN in 0.1% TFA/H2O over 20 mins to give 13 mg (42%) the title compound as a TFA salt. 1H NMR (400 MHz, CD3OD) δ 8.82 (s, 1H), 7.90 (dd, 1H), 7.70 (d, 1H), 7.62 (m, 3H), 7.34 (m, 3H), 6.60 (s, 1H), 3.92 (s, 3H). Diff Noe, irradiation at 3.92 ppm (N—CH3) enhanced 7.70 ppm (d, 1H, H-8). Mass spectrum (ESI, m/z) calcd. for C19H1BrN3O2 379.0, found 380.0 (M+H).

Workup

customThe compound was purified by RP-HPLC
washeluting with 30-70% CH3CN in 0.1% TFA/H2O over 20 mins

Sources & evidence

ORD record: ord-87070fa5170944d0a8ab2405837af5b5
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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