Dichloromethane → 21H,22H-Porphine

HRID 2220771Notes

Reaction equation

HRID 2220771 reaction equation
Br[C:2]1[C:3]2[NH:7][C:6]([C:8](C3C=CC=CC=3)=[C:9]3[N:32]=[C:12]([C:13](Br)=[C:14]4[NH:30][C:17](=[C:18](C5C=CC=CC=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.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+].C(Cl)Cl>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:3]12[CH:2]=[C:22]3[N:23]=[C:19]([CH:20]=[CH:21]3)[CH:18]=[C:17]3[NH:30][C:14]([CH:15]=[CH:16]3)=[CH:13][C:12]3=[N:32][C:9]([CH:10]=[CH:11]3)=[CH:8][C:6]([NH:7]1)=[CH:5][CH:4]=2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 178419281HCID 178419281, compound

Product 1

HCID 13770524121H,22H-Porphine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The general procedure was used to couple 5,15-dibromo-10,20-diphenylporphyrin (31.0 mg, 0.05 mmol) with (+)-dihydrocholesterol (77.8 mg, 0.2 mmol), using Pd2(dba)3 (4.6 mg, 0.005 mmol) and DPEphos (10.7 mg, 0.02 mmol) in the presence of Cs2CO3 (65.2 mg, 0.2 mmol). The reaction was conducted in toluene at 100° C. for 17 h. The title compound was isolated by flash chromatography (silica gel, methylene chloride: hexanes (v/v)=8:2) as a purple solid (27.5 mg, 45%). 1H NMR (300 MHz, CDCl3): δ 9.43 (d, J=4.8 Hz, 4H), 8.78 (d, J=4.8 Hz, 4H), 8.18 (m, 4H), 7.74 (m, 6H), 4.95 (s, 2H), 0.62-2.3 (m, 92H), −2.59 (s, 2H). UV-vis (CH2Cl2, λmax, nm): 418, 520, 557, 602, 660. HRMS-MALDI ([M+H]+): calcd for C86H115N4O2, 1235.9015, found 1235.90110 with an isotope distribution pattern that is the same as calculated one.

Sources & evidence

ORD record
ord-e49c8156b58249ef81b4391ffc65fa95
Source dataset
uspto-grants-2008_08
Patent number
US07417142B2

Reaction notes

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