Cesium carbonate → HCID 136037929, compound

HRID 2220782Notes

Reaction equation

HRID 2220782 reaction equation
Br[C:2]1[C:3]2[NH:7][C:6]([C:8]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:9]3[N:31]=[C:12]([CH:13]=[C:14]4[NH:30][C:17](=[C:18]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:19]5[CH:20]=[CH:21][C:22]=1[N:23]=5)[CH:16]=[CH:15]4)[CH:11]=[CH:10]3)=[CH:5][CH:4]=2.[CH:38]1[CH:43]=[C:42]2[CH:44]=[CH:45][C:46]([OH:59])=[C:47]([C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=[CH:50][C:49]=3[OH:58])[C:41]2=[CH:40][CH:39]=1.C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl>[C:24]1([C:18]2[C:19]3[CH:20]=[CH:21][C:22]([N:23]=3)=[C:2]([O:59][C:46]3[CH:45]=[CH:44][C:42]4[C:41](=[CH:40][CH:39]=[CH:38][CH:43]=4)[C:47]=3[C:48]3[C:49]([OH:58])=[CH:50][CH:51]=[C:52]4[C:57]=3[CH:56]=[CH:55][CH:54]=[CH:53]4)[C:3]3[NH:7][C:6]([C:8]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:9]4[N:31]=[C:12]([CH:13]=[C:14]5[NH:30][C:17]=2[CH:16]=[CH:15]5)[CH:11]=[CH:10]4)=[CH:5][CH:4]=3)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11762BinolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 173154257HCID 173154257, compound

Product 1

HCID 136037929HCID 136037929, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The general procedure was used to couple 5-bromo-10,20-diphenylporphin (54.2 mg, 0.1 mmol) with R-(+)-1,1′-Bi-2-naphthol (14.3 mg, 0.05 mmol), using Pd2(dba)3 (4.6 mg, 0.005 mmol) and DPEphos (10.8 mg, 0.02 mmol) in the presence of Cs2CO3 (37.6 mg, 0.1 mmol). The reaction was conducted in toluene at 100° C. for 24 h. The title compound was isolated by flash chromatography (silica gel, methylene chloride: hexanes (v/v)=8:2) as a purple-red solid (10 mg, 17%). 1H NMR (300 MHz, CDCl3) δ 10.12 (s, 1H), 9.27 (d, J=4.8 Hz, 4H), 8.97 (d, J=4.8 Hz, 4H), 8.78 (d, J=4.8 Hz, 4H), 8.17 (m, 4H), 7.99 (d, J=9.0 Hz, 1H), 7.94 (d, J=7.5 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.74 (m, 6H), 7.40-7.66 (m, 8H), 6.42 (d, J=9.6 Hz, 1H), −2.83 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 141.2, 134.7, 131.6, 131.0, 130.8, 130.4, 129.5, 128.6, 128.3, 127.9, 127.8, 127.6, 126.9, 125.2, 124.9, 124.6, 123.7, 119.8, 117.8, 117.2, 104.7, 88.5. UV-vis (CH2Cl2, λmax, nm): 414, 511, 545, 586, 641. HRMS-EI ([M]+): calcd for C52H34N4O2, 746.2682, found 746.2680.

Sources & evidence

ORD record
ord-0a3bb1358df548d4993d683b9e372d9d
Source dataset
uspto-grants-2008_08
Patent number
US07417142B2

Reaction notes

Loading…