5-(1-Phenylethyl)benzofuran-2-ylboronic acid → Methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate
Reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8]2)=[CH:4][C:3]=1[F:17].[C:18]1([CH:24]([C:26]2[CH:27]=[CH:28][C:29]3[O:33][C:32](B(O)O)=[CH:31][C:30]=3[CH:37]=2)[CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:3]1[CH:4]=[C:5]([CH2:6][N:7]2[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8]2)[CH:15]=[CH:16][C:2]=1[C:32]1[O:33][C:29]2[CH:28]=[CH:27][C:26]([CH:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:25])=[CH:37][C:30]=2[CH:31]=1Participants
Procedure
According to Scheme B2 and general procedure F, methyl 1-(4-bromo-3-fluorobenzyl)azetidine-3-carboxylate (0.241 g, 0.797 mmol) and 5-(1-phenylethyl)benzofuran-2-ylboronic acid (0.212 g, 0.797 mmol) were employed to give methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate. According to Scheme B2 and general procedure H, methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)-methyl)azetidine-3-carboxylate (0.275 g, 0.620 mmol) provided 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a white solid [hS1P1 EC50=99 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (t, J=8.0 Hz, 1H), 7.59 (s, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.20-7.35 (m, 8H), 7.12-7.20 (m, 1H), 4.28 (q, J=7.0 Hz, 1H), 3.60 (s, 2H), 3.18-3.46 (m, 5H), 1.64 (d, J=7.5 Hz, 3H). MS (ESI) m/z: Calculated: 429.2; Observed: 430.2 (M++1).
Sources & evidence
- ORD record
- ord-e5373923fbdd41d8a40ef3749173ed7e
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919519B2
Reaction notes
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