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

HRID 423486Notes

Reaction equation

HRID 423486 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:19][CH:18]=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>[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH:25]4[CH2:26][CH2:27][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]4)=[CH:21][CH:22]=3)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2773359(4-(Cyclopropylcarbamoyl)phenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777561-Methylethyl 4-[({4'-[(cyclopropylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylateYield 14.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (13 mg, 12%) was prepared from {4-[(cyclopropylamino)carbonyl]phenyl}boronic acid (41 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 7.77 (d, 2H, J=8.4 Hz), 7.59 (d, 2H, J=8.6 Hz), 7.53 (d, 2H, J=8.8 Hz), 6.96 (d, 2H, J=8.8 Hz), 6.24 (s, 1H), 4.97-4.84 (m, 1H), 4.21 (bs, 2H), 3.84 (d, 2H, J=6.4 Hz), 2.96-2.86 (m, 1H), 2.83-2.73 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.36-1.26 (m, 2H), 1.24 (d, 6H, J=6.4 Hz), 0.93-0.84 (m, 2H), 0.66-0.60 (m, 2H); LRMS (ESI), m/z 437 (M+H).

Sources & evidence

ORD record
ord-c38edae5b4064eb8b14d0f5bbfba54e4
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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