2-Methylpyridine-5-boronic acid → 2-(2-(1-(3-(6-Methylpyridin-3-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetic acid

HRID 1855099Notes

Reaction equation

HRID 1855099 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH2:14][C:11]([CH2:16][CH2:17][O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])([CH2:12][CH2:13]2)[CH2:10][O:9]3)[CH:5]=[CH:6][CH:7]=1.[CH3:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>>[CH3:27][C:28]1[N:33]=[CH:32][C:31]([O:1][C:2]2[CH:3]=[C:4]([C:8]34[CH2:15][CH2:14][C:11]([CH2:16][CH2:17][O:18][CH2:19][C:20]([OH:22])=[O:21])([CH2:12][CH2:13]3)[CH2:10][O:9]4)[CH:5]=[CH:6][CH:7]=2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 90408312tert-Butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate

Product 1

HCID 904086732-(2-(1-(3-(6-Methylpyridin-3-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetic acid

Procedure

Example 115 was synthesized using the same 2-step protocol as for the syntheses of Examples 39-45 from intermediate phenol 7F, but with 6-methylpyridin-3-ylboronic acid. LCMS, [M−H]+=396.2. 1H NMR (500 MHz, DMSO-d6) δ=8.18 (br. s, 1H), 7.35-7.25 (m, 3H), 7.11 (d, J=7.3 Hz, 1H), 7.00 (br. s, 1H), 6.83 (d, J=7.6 Hz, 1H), 3.95 (s, 2H), 3.58-3.43 (m, 2H), 2.44 (s, 3H), 2.06-1.96 (m, 2H), 1.81-1.72 (m, 2H), 1.68-1.54 (m, 4H), 1.40-1.34 (m, 2H), 1.28-1.20 (m, 2H).

Workup

  1. customExample 115 was synthesized

Sources & evidence

ORD record
ord-532decbfb5874e94aaa959980ae0b669
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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