3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 10018791, compound

HRID 2390387Notes

Reaction equation

HRID 2390387 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:6]=[CH:5]2.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)O1>>[N:15]1([CH2:14][CH2:13][O:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]=[C:2]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:11]=[CH:10]3)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 100416631-{2-[(6-bromo-2-naphthyl)oxy]ethyl}pyrrolidine

Product 1

HCID 10018791HCID 10018791, compound

Procedure

The product from Example 37B and 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine were processed as described in Example 38, except that a second column chromatography was done to provide 10 mg of the title compound. 1HNMR (300 MHz, CD3OD) δ 1.86 (m, 4H), 2.74 (m, 4H), 3.02 (t, 2H), 4.29 (t, 2H), 7.23 (dd, 1H), 7.31 (d, 1H), 7.56 (ddd, 1H), 7.76 (dd, 1H), 7.86-7.93 (m, 2H), 8.10 (d, 1H), 8.20 (ddd, 1H), 8.52 (dd, 1H), 8.91 (dd, 1H); MS (ESI) m/z 319 (M+H)+.

Sources & evidence

ORD record
ord-0f7c734eac1944b1b3456bf8275300b0
Source dataset
uspto-grants-2012_09
Patent number
US08273767B2

Reaction notes

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