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

HRID 1046168Notes

Reaction equation

HRID 1046168 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 66857463HCID 66857463, compoundHCID 66857543HCID 66857543, compound

Product 1

HCID 58109483HCID 58109483, compound

Procedure

Isomer 1 of the title compound, (S)-6-(4-fluorophenyl)-6-methyl-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one, was prepared from (S)-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=1.28, m/z=405 (M+1); 1H NMR (CDCl3) 8.84 (d, 1H, J=6.1 Hz), 7.81 (d, 1H, J=5.9 Hz), 7.75 (s, 1H), 7.70 (d, 2H, J=8.2 Hz), 7.52 (d, 2H, J=8.20 Hz), 7.34-7.31 (m, 2H), 7.09 (t, 2H, J=8.6 Hz), 5.81 (q, 1H, J=7.2 Hz), 2.89 (s, 3H), 2.84-2.72 (m, 2H), 2.31 (dt, 1H, J=13.9, 3.7 Hz), 2.11-2.03 (m, 1H), 1.64 (s, 3H), 1:38 (d, 3H, J=7 Hz).

Sources & evidence

ORD record
ord-b014271142254b6da377276592b70101
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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