Quinoline-3-boronic acid → (S)-2-tert-butoxy-2-(3-methyl-1-(quinolin-3-yl)naphthalen-2-yl)acetic acid

HRID 514018Notes

Reaction equation

HRID 514018 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].[N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29](B(O)O)[CH:28]=1>>[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:29]1[CH:28]=[N:27][C:36]2[C:31]([CH:30]=1)=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 56601711(S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 56601913(S)-2-tert-butoxy-2-(3-methyl-1-(quinolin-3-yl)naphthalen-2-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(3-methyl-1-(quinolin-3-yl)naphthalen-2-yl)acetic acid (16) was prepared following the procedure to make (S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid of Example 6, using quinolin-3-ylboronic acid instead of cyclohexenylboronic acid. The compound is an atropisomer mixture. 1H-NMR: 400 MHz, (CD3OD) δ: 9.20-8.50 (m, 2H), 8.18 (m, 1H), 8.08 (m, 1H), 7.95 (m, 1H), 7.80 (m, 3H), 7.40 (t. 1H), 7.25 (t, 1H), 7.06 (m, 1H), 5.19 (s, 1H), 2.62 (d, 3H), 0.95, 0.86 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C26H26NO3: 400.48. found: 400.2.

Sources & evidence

ORD record
ord-afdd80843dad492d80e1a7bc4f61bfca
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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