Potassium Bromide → {2-[3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1':3',1'']terphenyl-2'-yloxy]-ethoxy}acetic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14](=[O:33])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH:11]=[C:10]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[C:9]=2[O:41][CH2:42][CH2:43][O:44][CH2:45][C:46]([O:48]C)=[O:47])[CH:5]=[CH:6][CH:7]=1.[K+].[Br-]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14](=[O:33])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH:11]=[C:10]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[C:9]=2[O:41][CH2:42][CH2:43][O:44][CH2:45][C:46]([OH:48])=[O:47])[CH:5]=[CH:6][CH:7]=1Participants
Procedure
The title compound was prepared as a white foam (0.172 g, 47%) from {2-[3,3″-Dichloro-5′-(8-indol-1-yl-octylcarbamoyl)-[1,1′:3′,1″]terphenyl-2′-yloxy]-ethoxy}acetic acid, methyl ester using a procedure similar to step 4 of example 165; dec. >50° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.16–1.32 (m, 8H), 1.44–1.53 (m, 2H), 1.67–1.76 (m, 2H), 3.17–3.42 (m, 6H), 3.61 (s, 2H), 4.12 (t, J=7 Hz, 2H), 6.37 (d, J=3.1 Hz, 1H), 6.95–6.99 (m, 2H), 7.06–7.10 (m, 2H), 7.32 (m, 1H), 7.41–7.55 (m, 6H), 7.57–7.60 (m, 2H), 7.68–7.77 (m, 2H), 7.87 (s, 2H), 8.54 (t, J=5.5 Hz, 1H), 12.50 (broad s, 1H); IR (KBr) 3410, 2940, 1625, 1560, 1540, 1460, 1220, 1130 cm−1; mass spectrum [(+)APCI], m/z 687 (M+H)+; Anal. Calcd. for C39H40Cl2N2O5.0.5H2O: C, 67.24; H, 5.93; N, 4.02. Found: C, 67.26; H, 6.02; N, 3.96.
Workup
- custom>50° C.
Sources & evidence
- ORD record
- ord-777d7318f95f40c18c676ba017a1f5be
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07008636B2
Reaction notes
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