Cesium carbonate → HCID 136375619, compound

HRID 2220780Notes

Reaction equation

HRID 2220780 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.Cl.[CH3:39][O:40][C:41](=[O:51])[C@H:42]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[NH2:43].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+]>C1COCC1.C(Cl)Cl>[CH3:39][O:40][C:41](=[O:51])[CH:42]([NH:43][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)[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 173154257HCID 173154257, compound

Product 1

HCID 136375619HCID 136375619, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The general procedure was used to couple 5-bromo-10,20-diphenylporphin (27.1 mg, 0.05 mmol) with (L)-phenylalanine methyl ester hydrochloride (43 mg, 0.2 mmol), using Pd (OAc)2 (1.12 mg, 0.005 mmol) and DPEphos (5.38 mg, 0.01 mmol) in the presence of Cs2CO3 (65.2 mg, 0.2 mmol). The reaction was conducted in THF 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 (12 mg, 36%). 1H NMR (300 MHz, CDCl3) δ 9.79 (s, 1H), 9.14 (d, J=4.8 Hz, 1H), 9.09 (d, J=4.8 Hz, 1H), 8.84 (d, J=4.8 Hz, 1H), 9.28 (d, J=4.8 Hz, 1H), 9.01-9.06 (m, 3H), 8.98 (d, J=4.8 Hz, 1H), 8.67 (d, J=4.8 Hz, 2H), 8.18 (m,4H), 7.77 (m, 6H), 7.49 (dd, J=1.5, 8.4 Hz, 2H), 7.34-7.43 (m, 3H), 6.60 (d, bro., 1H), 5.52 (d, bro, 1H), 3.63 (t, J=6.9 Hz, 1H), 3.32 (s, 3H), 2.16 (s, 2H), −2.32 (s, 2H); 13C NMR (CDCl3, 75 MHz) δ 174.2, 141.7, 136.8, 134.5, 131.8, 130.8, 129.8, 128.8, 128.5, 127.6, 127.2, 126.8, 126.1, 119.4, 102.2, 72.1, 51.7, 40.8. UV-vis (CH2Cl2, λmax, nm): 420, 521, 562, 660. HRMS-MALDI ([M+H]+): calcd for C42H34N5O2, 640.2707; found: 640.2714.

Sources & evidence

ORD record
ord-82ccc9f08df4470fae3c8472940643a1
Source dataset
uspto-grants-2008_08
Patent number
US07417142B2

Reaction notes

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