4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(9-Bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid
Reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.Cl[S:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=1)(=[O:32])=[O:31]>>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][S:30]([C:33]3[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=3)(=[O:32])=[O:31])=[C:19]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2Participants
Procedure
Using 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenol (0.289 g, 0.641 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.717 g, 3.03 mmol) the title compound was prepared according to the procedure in Example 1, step 9. Purification on Dynamax C18 eluting with 100% CH3CN (0.1% TFA added) gave 0.25 g (60%) of the title compound as a yellow solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.31-1.36 (m, 2 H), 1.49-1.59 (m, 5 H), 1.61-1.63 (m, 3 H), 1.78-1.82 (m, 1 H), 2.44 (s, 3 H), 3.04-3.10 (m, 1 H), 7.25-7.31 (m, 3 H), 7.34-7.37 (m, 3 H), 7.50 (t, 1 H), 7.66 (t, 1 H), 8.02 (d, 1 H), 8.21 (d, 1 H). IR (KBr): 3425, 2900, 1650, 1400 and 1175 cm-1. mass spectrum (-ESI), m/z 649/651 (M-H). Anal. Calcd. for C32H27BrO6S2.0.6H2O: C, 58.02; H, 4.29 N, 0.00. Found: C, 57.98; H, 4.35 N, 0.10.
Sources & evidence
- ORD record
- ord-658ad56894b741c9816fcf7c9a2debe0
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121271
Reaction notes
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