Sodium Carbonate → 1,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423537Notes

Reaction equation

HRID 423537 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[N:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 59718534tert-Butyl 4-{[(6-chloropyridin-3-yl)oxy]methyl}piperidine-1-carboxylate

Product 1

HCID 249943331,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (6.87 g, 88%) was prepared as a gray solid from 1,1-dimethylethyl 4-{[(6-chloro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 73, Step 1, 5.73 g, 17.5 mmol), [4-(methylsulfonyl)phenyl]boronic acid (3.85 g, 17.53 mmol), Pd(PPh3)4 (10.13 g, 8.76 mmol), 2M Na2CO3 (26 mL) in DME (170 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CDCl3): δ 8.40 (d, 1H, J=2.9 Hz), 8.15-8.12 (m, 2H), 8.02-7.99 (m, 2H), 7.73 (d, 1H, J=8.7 Hz), 7.28 (dd, 1H, Ja=8.7 Hz, Jb=3.0 Hz), 4.19 (bs, 2H), 3.91 (d, 2H, J=6.4 Hz), 3.08 (s, 3H), 2.81-2.71 (m, 2H), 2.07-1.96 (m, 1H), 1.87-1.82 (m, 2H), 1.47 (s, 9H), 1.36-1.24 (m, 2H); LRMS (APCI), m/z 447 (M+H).

Sources & evidence

ORD record
ord-db067f9670de4d2fbe99a350b9dcaa93
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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