6-(Adamantan-1-ylmethoxy)-5-chloronicotinic acid → Methyl 5-chloro-2-fluoro-4-((3,5,7-trifluoroadamantan-1-yl)methoxy)benzoate
Reaction equation
[C:1]12(COC3C(Cl)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[Cl:23][C:24]1[C:25]([O:34][CH2:35][C:36]23[CH2:46][C:40]4([F:47])[CH2:41][C:42]([F:45])([CH2:44][C:38]([F:48])([CH2:39]4)[CH2:37]2)[CH2:43]3)=[CH:26][C:27]([F:33])=[C:28]([CH:32]=1)[C:29]([OH:31])=[O:30]>>[Cl:23][C:24]1[C:25]([O:34][CH2:35][C:36]23[CH2:46][C:40]4([F:47])[CH2:41][C:42]([F:45])([CH2:44][C:38]([F:48])([CH2:39]4)[CH2:37]2)[CH2:43]3)=[CH:26][C:27]([F:33])=[C:28]([CH:32]=1)[C:29]([O:31][CH3:1])=[O:30]Participants
3
Procedure
Following the procedure as described in Example 150 step 2 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-chloronicotinic acid with 5-chloro-2-fluoro-4-((−3,5,7-trifluoroadamantan-1-yl)methoxy)benzoic acid, the title compound was obtained as a colorless solid (0.90 g, quant.): 1H NMR (300 MHz, CDCl3) δ 7.96 (d, J=7.5 Hz, 1H), 6.62 (d, J=12.0 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 2H), 2.24-2.05 (m, 6H), 1.87-1.78 (m, 6H); MS (ES+) m/z 407.3, 409.1 (M+1).
Sources & evidence
- ORD record
- ord-474af0ccb68241ecbe3c5a3b1218428b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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