(5-Fluoropyridin-3-yl)boronic acid → HCID 58109724, compound

HRID 1046118Notes

Reaction equation

HRID 1046118 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[N:32][CH:33]=1>>[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:30]3[CH:31]=[N:32][CH:33]=[C:28]([F:27])[CH:29]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 53473487(R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

Product 1

HCID 58109724HCID 58109724, compound

Procedure

The title compound was prepared from (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one and 5-fluoropyridine-3-boronic acid following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.84 min, m/z=435 (M+1); 1H NMR (CDCl3) 8.58 (t, 1H, J=1.5, 1.5 Hz), 8.44 (d, 1H, J=3 Hz), 7.51-7.48 (ddd, 1H, J=9, 4, 2 Hz), 7.33-7.262 (m, 4H), 7.04 (at, J=9, 9 Hz), 6.98 (d, 2H, 8 Hz), 5.76-5.66 (m, 2H), 5.11-5.00 (m, 2H), 3.00-2.95 (m, 1H), 2.65-2.5 (m, 2H), 2.41-2.33 (m, 1H) 2.31-2.18 (m, 2H), 1.55 (d, 3H, J=7 Hz).

Sources & evidence

ORD record
ord-bac43a8d155544e09b6e7a44864d8fd6
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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