Cyclopropylboronic acid → tert-butyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-((E)-prop-1-en-1-yl)benzoate
Reaction equation
O1[C:5]2([CH2:10]CC(COC3C(Cl)=CC(C(OC(C)(C)C)=O)=C(F)C=3)C[CH2:6]2)OCC1.[C:28]12([CH2:38][O:39][C:40]3[C:52](Cl)=[CH:51][C:43]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[C:42]([F:54])[CH:41]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2.C1(B(O)O)CC1.C(/B1OC(C)(C)C(C)(C)O1)=C\C>>[C:28]12([CH2:38][O:39][C:40]3[C:52](/[CH:6]=[CH:5]/[CH3:10])=[CH:51][C:43]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[C:42]([F:54])[CH:41]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 305/306 Step 2 and making variations as required to replace tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-ylmethoxy)-5-chloro-2-fluorobenzoate with tert-butyl 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoate and to replace cyclopropylboronic acid with trans-propenylboronic acid pinacol ester, tert-butyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-((E)-prop-1-en-1-yl)benzoate was obtained as a yellowish oil (1.20 g, quant.). To a mixture of tert-butyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-((E)-prop-1-en-1-yl)benzoate (0.30 g, 0.75 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL) and the reaction mixture was stirred at ambient temperature for 2 hours. Concentration in vacuo gave the title compound as a yellowish residue (0.260 g, quant.) which was used without further purification: MS (ES+) m/z 345.2 (M+1).
Sources & evidence
- ORD record
- ord-a467efeb3eae44c598c2dba311d7f638
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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