Potassium Carbonate → HCID 86628044, compound

HRID 2078413Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[F:13].[C:14]([O:18][C:19]([N:21]1[CH2:28][CH:27]2[O:29][CH:23]([CH2:24][NH:25][CH2:26]2)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH:23]2[O:29][CH:27]([CH2:26][NH:25][CH2:24]2)[CH:28]1[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[F:13])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-(2-bromoethoxy)-3-fluorobenzonitrile (21.6 g, 0.0885 mol; see step (v) above), 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (21.1 g, 0.07965 mol; see WO 01/28992) and dry K2CO3 (48.9 g, 0.354 mol) in 200 mL of dry acetonitrile was stirred at 60° C. for five days under a nitrogen atmosphere. The reaction mixture was filtered through Celite® and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 27% ethyl acetate in petroleum ether as eluent, to yield 20.5 g of the sub-title compound as a solid.

Workup

filtrationThe reaction mixture was filtered through Celite®
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record: ord-2b3018f2d1be4cacbd93e45d109bc1a7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928225B2

Reaction notes

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