Cesium carbonate → HCID 59752648, compound

HRID 2106233Notes

Reaction equation

HRID 2106233 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[NH:14][N:13]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[N+:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br)([O-:27])=[O:26].C([O-])([O-])=O.[Cs+].[Cs+]>>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:17][CH2:16][C:15]=3[N:14]([CH2:31][C:30]3[CH:33]=[CH:34][CH:35]=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=3)[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester

Product 1

HCID 59752648HCID 59752648, compoundYield 4.5%

Procedure

The title compound (0.005 g) was prepared from 3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 59, Step C, 0.1 g) using 3-nitrobenzyl bromide (0.09 g) in place of benzyl chloride and Cs2CO3 (0.2 g) in place of NaH. MS (ESI): exact mass calculated for C20H19ClN4O2, 382.12; found, m/z 383.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.07-8.05 (m, 1H), 7.91-7.87 (m, 1H), 7.50 (t, J=7.9 Hz, 1H), 7.44-7.38 (m, 3H), 7.36-7.33 (m, 2H), 5.41 (s, 2H), 2.88-2.85 (m, 4H), 2.82-2.79 (m, 2H), 2.73-2.71 (m, 2H).

Sources & evidence

ORD record
ord-a530687be1f245a18cdbc664f29759b1
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

Loading…