Aniline → HCID 135474506, compound

HRID 2220769Notes

Reaction equation

HRID 2220769 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.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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.P.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:39]1([NH:38][C:2]2[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](=[C:18]([C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)[C:19]6[CH:20]=[CH:21][C:22]=2[N:23]=6)[CH:16]=[CH:15]5)[CH:11]=[CH:10]4)=[CH:5][CH:4]=3)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 5

HCID 6115AnilineHCID 10796Cesium carbonateHCID 24404PhosphineHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 173154257HCID 173154257, compound

Product 1

HCID 135474506HCID 135474506, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The general procedure was used to couple 5-bromo-10,20-diphenylporphyrin (27 mg, 0.05 mmol) with aniline (17 μL, 0.18 mmol), using palladium acetate (0.55 mg, 0.0025 mmol) as the palledium precursor, DPEphos (2.0 mg, 0.0038 mmol) as the phosphine ligand and cesium carbonate (22.8 mg, 0.070 mmol) as the base. The reaction was conducted in THF (5 mL) at 68° C. for 19 h. The title compound was isolated by flash chromatography (silica gel, ethyl acetate:hexanes (v)=1:4) as red solids (27 mg, 98%). 1H NMR (300 MHz, THF-d8): δ 10.14 (s, 1H), 9.44 (d, J=4.8 Hz, 2H), 9.42 (s, 1H), 9.30 (d, J=4.8 Hz, 2H), 8.90 (d, J=4.8 Hz, 2H), 8.77 (d, J=4.8 Hz, 2H), 8.21 (m, 4H), 7.78 (m, 6H), 7.06 (t, J=7.4, 2H), 6.86 (d, J=7.4 Hz, 2H), 6.69 (J=7.4 Hz, 1H), −2.54 (s, 2H). 13C NMR (75 MHz, THF-d8): δ 154.8, 147.7, 142.7, 135.5, 132.1, 131.9, 131.1, 129.7, 128.5, 127.7, 120.6, 120.1, 119.0, 115.5, 105.1. IR (film, cm−1): 3302, 3043, 1599, 1495, 1476, 1338, 1309, 1255, 1064, 973, 958, 797, 748. UV-vis(THF, λmax, nm): 412, 512, 582, 660. HRMS-EI ([M]+): calcd for C38H27N5, 553.2266; found: 553.2274 with an isotope distribution pattern that is same as the calculated one.

Sources & evidence

ORD record
ord-cb903c681914481fb17bce9ae59681e0
Source dataset
uspto-grants-2008_08
Patent number
US07417142B2

Reaction notes

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