Methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate → 4-((3-(((Tert-butyldimethylsilyl)oxy)methyl)adamantan-1-yl)methoxy)-5-chloro-2-fluorobenzoic acid
Reaction equation
C12(COC3C(C4CC4)=CC(C(OC)=O)=CN=3)CC3CC(CC(C3)C1)C2.[Si:26]([O:33][CH2:34][C:35]12[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43][C:37]([CH2:45][O:46][C:47]4[C:56]([Cl:57])=[CH:55][C:50]([C:51]([O:53]C)=[O:52])=[C:49]([F:58])[CH:48]=4)([CH2:38]3)[CH2:36]1)[CH2:42]2)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>>[Si:26]([O:33][CH2:34][C:35]12[CH2:42][CH:41]3[CH2:40][CH:39]([CH2:38][C:37]([CH2:45][O:46][C:47]4[C:56]([Cl:57])=[CH:55][C:50]([C:51]([OH:53])=[O:52])=[C:49]([F:58])[CH:48]=4)([CH2:43]3)[CH2:36]1)[CH2:44]2)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in Example 150 step 4 and making variations as required to replace methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate with methyl 4-((3-(((tert-butyldimethylsilyl)oxy)methyl)adamantan-1-yl)methoxy)-5-chloro-2-fluorobenzoate, the title compound was obtained as a colorless solid (1.02 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 13.03 (br s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.12 (d, J=12.7 Hz, 1H), 3.70 (s, 2H), 3.12 (s, 2H), 2.05-1.96 (m, 2H), 1.63-1.42 (m, 6H), 1.41-1.27 (m, 6H), 0.81 (s, 9H), −0.05 (s, 6H); MS (ES+) m/z 483.1, 485.1 (M+1).
Sources & evidence
- ORD record
- ord-5007e9e6f461423eb61feb025a6b8a56
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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