2-Methylpyridine-4-boronic acid → HCID 58109483, compound

HRID 1046169Notes

Reaction equation

HRID 1046169 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH3:30])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.BrC1C=CC([C@@H](N2CC[C@@](C3C=CC(F)=CC=3)(C)OC2=O)C)=CC=1.CC1C=C(B(O)O)C=CN=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:30])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 41926642-Methylpyridine-4-boronic acidHCID 66857642HCID 66857642, compoundHCID 66858187HCID 66858187, compound

Product 1

HCID 58109483HCID 58109483, compound

Procedure

Isomer 2 of the title compound, (R)-6-(4-fluorophenyl)-6-methyl-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one, was prepared from (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-methyl-1,3-oxazinan-2-one and 2-methylpyridine-4-boronic acid following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.18, m/z=405 (M+1); 1H NMR (CDCl3) 8.83 (s, 1H), 7.72 (s, 1H), 7.66 (s, 1H), 7.48 (d, 2H, J=7.3 Hz), 7.32 (br m, 2H), 7.16 (d, 2H, J=6.7), 7.04 (t, 2H, J=7.6 Hz), 5.77 (q, 1H, J=6.7 Hz), 3.05 (br m, 1H), 2.89 (s, 3H, 2.42-2.32 (m, 2H), 2.23 (br m, 1H), 1.64 (s, 3H), 1.59 (d, 3H, J=6.7 Hz).

Sources & evidence

ORD record
ord-1b29d3d7b0ef4cdca4a93a0e8973770c
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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