Toluene → HCID 58611952, compound

HRID 751267Notes

Reaction equation

C[Al](C)C.C1(C)C=CC=CC=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C([O:20][C:21](=O)[CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]2[CH:32]=1)C>ClCCl.[Cl-].[NH4+]>[Br:31][C:28]1[CH:29]=[CH:30][C:25]2[N:26]([CH:32]=[C:23]([CH2:22][C:21]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[O:20])[N:24]=2)[CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Add 2M trimethylaluminum in toluene (1.94 mL, 3.88 mmol) to a solution of morpholine (0.34 g, 3.88 mmol) in dichloromethane (10 mL). Stir for 10 min and add a solution of (6-bromo-imidazo[1,2-a]pyridin-2-yl)-acetic acid ethyl ester (1.1 g, 3.88 mmol) in dichloromethane (12 mL). Heat at 40° C. for 1 h, carefully dilute with saturated aqueous ammonium chloride and extract into dichloromethane. Concentration followed by filtration gives the titled compound (0.55 g, 43%) as a white solid. TOF MS ES+ exact mass calculated for C13H14BrN3O2 (p+1): m/z=324.0348; Found: 324.0330. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (m, 1H), 7.77 (s, 1H), 7.45 (d, J=10 Hz, 1H), 7.29 (dd, J=10, 2.0 Hz, 1H), 3.81 (s, 2H), 3.55-3.4 (m, 8H).

Workup

extractionextract into dichloromethane
concentrationConcentration
filtrationfollowed by filtration

Sources & evidence

ORD record: ord-c4bb8573c34c47db94031d57c331ed61
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405299B2

Reaction notes

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