Sodium Carbonate → HCID 66673173, compound

HRID 423539Notes

Reaction equation

HRID 423539 reaction equation
Br[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][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26])[CH3:23].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>[CH3:20][CH:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][O:8][C:5]2[CH:6]=[N:7][C:2]([C:30]3[CH:31]=[CH:32][C:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])=[CH:28][CH:29]=3)=[CH:3][CH:4]=2)[CH2:11][CH2:12]1)=[O:17])[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 66673173HCID 66673173, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Methylethyl-4-{[(6-{4-[(ethyloxy)carbonyl]phenyl}-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate was prepared as an off-white solid from 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 0.13 g, 0.67 mmol), {4-[(ethyloxy)carbonyl]phenyl}boronic acid (0.30 g, 0.84 mmol), 2M Na2CO3 (10 mL) and Pd(PPh3)4 (0.01 g, 0.01 mmol) in DME (10 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CDCl3): δ 8.39 (d, 1H, J=2.7 Hz), 8.11 (d, 2H, J=8.6 Hz), 7.98 (d, 2H, J=8.6 Hz), 7.72 (d, 1H, J=8.8 Hz), 7.31-7.26 (m, 1H), 4.94-4.87 (m, 1H), 4.38 (q, 2H, J=7.1 Hz), 4.28-4.16 (m, 2H), 3.89 (d, 2H, J=6.4 Hz), 2.82-2.72 (m, 2H), 2.06-1.94 (m, 1H), 1.87-1.80 (m, 4H), 1.39 (t, 3H, J=7.1 Hz), 1.23 (d, 6H, J=6.4 Hz); LRMS (ESI), m/z 427 (M+H).

Sources & evidence

ORD record
ord-249bdce88bee4774a3c22faaa2ed14f3
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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