Sodium Carbonate → HCID 66673129, compound

HRID 423578Notes

Reaction equation

HRID 423578 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]3)=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 66673129HCID 66673129, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Methylethyl 4-[({6-[4-(hydroxymethyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (208 mg, 77%) was prepared as a white solid from 4-(hydroxy methyl)phenylboronic acid (130 mg, 0.84 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 250 mg, 0.70 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (4 mL) and DME (4 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.37 (bs, 1H), 7.94 (d, 2H, J=7.9 Hz), 7.70 (d, 1H, J=8.6 Hz), 7.46 (d, 2H, J=8.1 Hz), 7.45-7.30 (bs, 1H), 4.91 (septet, 1H, J=6.2 Hz), 4.74 (s, 2H), 4.21 (bs, 2H), 3.90 (d, 2H, J=6.2 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 385 (M+H).

Sources & evidence

ORD record
ord-12efc6cf389a4290b81ebc9c3772267f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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