3-Formylphenylboronic acid → [3,3''-Diformyl-5'-(8-phenyl-octylcarbamoyl)-[1,1';3'1'']terphenyl-2'-yl]methyl ether

HRID 1281400Notes

Reaction equation

HRID 1281400 reaction equation
[CH3:1][O:2][C:3]1[C:8](I)=[CH:7][C:6]([C:10](=[O:26])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:5][C:4]=1I.[CH:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)=[O:29]>>[CH:28]([C:30]1[CH:31]=[C:32]([C:4]2[CH:5]=[C:6]([C:10](=[O:26])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:7]=[C:8]([C:4]3[CH:3]=[CH:8][CH:7]=[C:6]([CH:10]=[O:26])[CH:5]=3)[C:3]=2[O:2][CH3:1])[CH:33]=[CH:34][CH:35]=1)=[O:29]

Participants

3

Reactant 2

HCID 27343563-Formylphenylboronic acidHCID 222375512,6-Diiodo-4-(8-phenyl-octylcarbamoyl)phenyl methyl ether

Product 1

HCID 131722494[3,3''-Diformyl-5'-(8-phenyl-octylcarbamoyl)-[1,1';3'1'']terphenyl-2'-yl]methyl ether

Procedure

The title compound was prepared as a solid (0.479 g, 75%) from 2,6-diiodo-4-(8-phenyl-octylcarbamoyl)phenyl methyl ether using 3-formylbenzeneboronic acid and a procedure similar to step 3 of Example 93; 1H NMR (DMSO-d6) δ 1.21-1.35 (m, 8H), 1.46-1.60 (m, 4H), 2.47-2.58 (m, 2H), 3.13 (s, 3H), 3.21-3.32 (m, 2H), 7.09-7.19 (m, 3H), 7.21-7.30 (m, 2H), 7.54 (t, J=7.5 Hz, 2H), 7.94-8.03 (m, 6H), 8.17 (s, 2H), 8.61 (t, J=5.6 Hz, 1H), 10.14 (s, 2H); mass spectrum [(+) ESI], m/z 548 (M+H)+, 570 (M+Na)+.

Sources & evidence

ORD record
ord-60ae982ae87d40e6a8fd0b1bf05ec967
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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