Sodium Carbonate → 1-Methylethyl 4-({[4'-(4-morpholinylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423492Notes

Reaction equation

HRID 423492 reaction equation
[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[CH:22][CH:21]=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>[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH:28]4[CH2:29][CH2:30][N:31]([C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]4)=[CH:24][CH:25]=3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441195464-(Morpholin-4-ylsulphonyl)benzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777741-Methylethyl 4-({[4'-(4-morpholinylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 9.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (10 mg, 8%) was prepared as a white solid from [4-(4-morpholinylsulfonyl)phenyl]boronic acid (54 mg, 0.2 mmol), 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) in a manner similar to Example 21, Step 3, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.78 (m, 2H), 7.70 (m, 2H), 7.54 (d, 2H, J=8.8 Hz), 6.99 (d, 2H, J=8.8 Hz), 4.97-4.86 (m, 1H), 4.22 (bs, 2H), 3.86 (d, 2H, J=6.4 Hz), 3.78-3.73 (m, 4H), 3.07-3.01 (m, 4H), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.91-1.81 (m, 2H), 1.37-1.27 (m, 2H), 1.25 (d, 6H, J=6.4 Hz); LRMS (ESI), m/z 503 (M+H).

Sources & evidence

ORD record
ord-1b82fac44c1640178540be4ac8e34015
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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