4-Fluorophenylboronic acid → (5R*,6S*)-3-(3,5-Dichlorophenyl)-6-(4'-fluorobiphenyl-4-yl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione

HRID 1792872Notes

Reaction equation

HRID 1792872 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:27][CH2:26][CH2:25][C@:9]32[N:13]([CH3:14])[C:12](=[O:15])[N:11]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[C:10]3=[O:24])=[CH:4][CH:3]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[Cl:23][C:18]1[CH:17]=[C:16]([N:11]2[C:10](=[O:24])[C@:9]3([CH2:25][CH2:26][CH2:27][C@H:8]3[C:5]3[CH:6]=[CH:7][C:2]([C:32]4[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=4)=[CH:3][CH:4]=3)[N:13]([CH3:14])[C:12]2=[O:15])[CH:21]=[C:20]([Cl:22])[CH:19]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 60054691(5R*,6S*)-6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione

Product 1

HCID 60054806(5R*,6S*)-3-(3,5-Dichlorophenyl)-6-(4'-fluorobiphenyl-4-yl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dioneYield 14.6%

Procedure

Using the procedure described in Example 8 (5R*,6S*)-6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (80 mg, 0.17 mmol) (Example 1) was reacted with 4-fluorophenylboronic acid (71.4 mg, 0.51 mmol) to yield the above-titled compound (12 mg) as a white solid. 1H NMR (CDCl3) δ 7.45–7.55 (4H, m), 7.05–7.25 (5H, m), 6.62 (2H, m), 3.46 (1H, dd, J1=12.9 Hz, J2=6.3 Hz), 3.18 (3H, s), 2.5–2.75 (1H, m), 1.85–2.45 (5H, m).

Sources & evidence

ORD record
ord-439a77c73ae7453d917a074aa8cfea94
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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