Pyridine → HCID 69196730, compound

HRID 2220227Notes

Reaction equation

HRID 2220227 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[NH:8][CH2:7][C:6]=2[CH:18]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[N:8]([C:19](=[O:21])[CH3:20])[CH2:7][C:6]=2[CH:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68965888HCID 68965888, compound2×

Product 1

HCID 69196730HCID 69196730, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 9-Bromo-2-chloro-11,12-dihydro-6H-5-oxa-12-aza-dibenzo[a,e]cyclooctene Example 347E (3.8 mg, 11.7 umol) and DMAP (cat. amount) in toluene (0.3 mL) was added acetic anhydride (0.10 mL, 1.05 mmol) and pyridine (0.05 mL, 46.9 umol). This reaction mixture was heated at 70° C. for 30 minutes, cooled to room temperature and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 4 g column, eluted with Hexane-CH2Cl2, detected at 220 nM to give 4.1 mg of 1-(9-Bromo-2-chloro-6,11-dihydro-5-oxa-12-aza-dibenzo[a,e]cycloocten-12-yl)-ethanone Example 347E in 96% yield. HPLC Rt=3.56 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=366.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThis was purified by a ISCO auto CombiFlash with a RediSep 4 g column
  4. washeluted with Hexane-CH2Cl2

Sources & evidence

ORD record
ord-67ef38d3a57b4dddaf15e8a29a8693da
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

Loading…