Phenylboronic Acid → (4r)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane

HRID 1878649Notes

Reaction equation

HRID 1878649 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.BrC1[CH:14]=[CH:15][C:16]([O:19][C@H:20]2[CH:27]3[CH2:28][N:23]4[CH2:24][CH:25]([CH2:29][CH:21]2[CH2:22]4)[CH2:26]3)=[N:17][CH:18]=1.C1(B(O)O)C=CC=CC=1>>[C:1]1([C:11]2[CH:14]=[CH:15][C:16]([O:19][C@H:20]3[CH:27]4[CH2:28][N:23]5[CH2:24][CH:25]([CH2:29][CH:21]3[CH2:22]5)[CH2:26]4)=[N:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 86621321(4r)-4-(5-Bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

Product 1

HCID 86621320(4r)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane

Procedure

Prepared from the product of Example 9F (496 mg, 1.60 mmol) and phenylboronic acid (480 mg, 3.1 mmol; Aldrich) according to Method B: 1H NMR (300 MHz, methanol-D4) δ ppm 1.75 (s, 1H), 2.00-2.25 (m, 6H), 2.98 (d, J=12.9 Hz, 2H), 3.15 (s, 2H), 3.51 (d, J=12.9 Hz, 2H), 5.33 (s, 1H), 6.90-6.96 (m, 1H), 7.30-7.38 (m, 1H), 7.40-7.48 (m, 2H), 7.54-761 (m, 2H), 7.94 (dd, J=8.6, 2.5 Hz, 1H), 8.35 (d, J=2.4 Hz, 1H), MS (ESI) m/z=307 (M+H)+.

Sources & evidence

ORD record
ord-9c96dc9342e54955963dec4d7ab23933
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

Loading…