Trifluoroacetic acid → 4-(5-(((4-Phenylpiperidin-4-yl)methoxy)methyl)pyridine-3yl)benzonitrile

HRID 656519Notes

Reaction equation

HRID 656519 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][O:9][CH2:10][C:11]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:7]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)#[N:24].C(O)(C(F)(F)F)=O>>[C:17]1([C:11]2([CH2:10][O:9][CH2:8][C:6]3[CH:7]=[C:2]([C:28]4[CH:29]=[CH:30][C:25]([C:23]#[N:24])=[CH:26][CH:27]=4)[CH:3]=[N:4][CH:5]=3)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27343264-Cyanophenylboronic acidHCID 248009253-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine

Product 1

HCID 248009264-(5-(((4-Phenylpiperidin-4-yl)methoxy)methyl)pyridine-3yl)benzonitrileYield 64%

Procedure

This compound was prepared according to the experimental condition of Example 1 method A from 3-bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine (75 mg, 0.16 mmoL), and 4-cyanobenzene boronic acid (90 mg, 0.64 mmol) to afford 50.0 mg (64%) of the desired compound as its TFA salt. 1H-NMR (CD3OD, 400 MHz) δ 8.99 (s, 1H), 8.52 (s, 1H), 8.25 (s, 1H), 7.92 (d, 2H, J=7.2 Hz), 7.83 (d, 2H, J=7.2 Hz), 7.21-7.46 (m, 5H), 4.64 (s, 2H), 3.58 (s, 2H), 3.32-3.60 (m, 2H), 2.89-2.96 (m, 2H), 2.51-2.56 (m, 2H), 2.21-2.22 (m, 2H). Mass spec.: 384.14 (MH)−.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-88b94d276d47423dba8eca1ab6eb6777
Source dataset
uspto-grants-2011_12
Patent number
US08071778B2

Reaction notes

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