(5-Fluoroquinolin-8-yl)boronic acid → (2S)-2-tert-butoxy-2-(1-(5-fluoroquinolin-8-yl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514011Notes

Reaction equation

HRID 514011 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1C1CCCCC=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]1[CH:37]=[CH:36][C:35](B(O)O)=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[N:33]2>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:35]1[CH:36]=[CH:37][C:28]([F:27])=[C:29]2[C:34]=1[N:33]=[CH:32][CH:31]=[CH:30]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 46739102(5-Fluoroquinolin-8-yl)boronic acidHCID 56601711(S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 56601712(2S)-2-tert-butoxy-2-(1-(5-fluoroquinolin-8-yl)-3-methylnaphthalen-2-yl)acetic acid

Procedure

(2S)-2-tert-Butoxy-2-(1-(5-fluoroquinolin-8-yl)-3-methylnaphthalen-2-yl)acetic acid (10) was prepared following the procedure to make (S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid of Example 6 except 5-fluoroquinolin-8-ylboronic acid was used instead of cyclohexenylboronic acid. 1H-NMR: 400 MHz, (CD3OD) δ: 8.81 (d, J=8.2 Hz, 1H), 8.70 (dd, J=3.3 Hz, J=4.7 Hz,1H), 8.09 (t, J=6.2 Hz, 1H), 7.92 (m, 2H), 7.78 (m, 1H), 7.63 (t, J=9.0 Hz, 1H), 7.42 (t, J=7.0 Hz, 1H), 7.18 (t, J=7.8 Hz,1H), 6.84 (d, J=7.6 Hz, 1H), 5.18 (s, 1H), 2.68 (s, 3H), 0.80 (s, 9H). 19F-NMR: 377 MHz, (CD3OD) δ: −77.9, −123.2. LCMS-ESI+ (m/z): [M+H]+ calcd for C26H25FNO3: 418.47. found: 418.1.

Sources & evidence

ORD record
ord-df2e14c550fd42da91d27482a0dc3c2f
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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