3-Bromo-9H-xanthen-9-one → N,N-Diethyl-9-oxo-9H-xanthene-3-carboxamide

HRID 733391Notes

Reaction equation

HRID 733391 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C([O:21][C:22]([N:24]1[CH:29]2CC[CH:25]1[CH2:26]C(=O)[CH2:28]2)=O)(C)(C)C.[Br:33][C:34]1[CH:35]=[CH:36][C:37]2[C:38](=[C:48]3[CH2:54][CH:53]4[NH:55][CH:50]([CH2:51][CH2:52]4)[CH2:49]3)[C:39]3[C:44]([O:45][C:46]=2[CH:47]=1)=[CH:43][CH:42]=[CH:41][CH:40]=3>>[CH2:25]([N:24]([CH2:29][CH3:28])[C:22]([C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:21])[CH3:26].[Br:33][C:34]1[CH:35]=[CH:36][C:37]2[C:38](=[C:48]3[CH2:54][CH:53]4[NH:55][CH:50]([CH2:51][CH2:52]4)[CH2:49]3)[C:39]3[C:44]([O:45][C:46]=2[CH:47]=1)=[CH:43][CH:42]=[CH:41][CH:40]=3

Participants

5

Reactant 3

HCID 2316083-Bromo-9H-xanthen-9-one2×HCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 578392193-(3-Bromo-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]octane2×

Product 2

HCID 15953972N,N-Diethyl-9-oxo-9H-xanthene-3-carboxamideHCID 578392193-(3-Bromo-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]octane

Procedure

Using an adaptation of the method described in Procedure 7, substituting 3-bromo-xanthen-9-one, 3a, for 9-oxo-9H-xanthene-3-carboxylic acid diethylamide, 6a (13.69, 46 mmol) and 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester for N-carbethoxynortropinone, the title compound 3-(3-bromo-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]octane, 1b was obtained. MS m/z (MH+) 368.0/370.0

Sources & evidence

ORD record
ord-97bfd32f7ee942128f62c81346f703dd
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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