Water → HCID 66673094, compound

HRID 423661Notes

Reaction equation

HRID 423661 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:14]1[N:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].O>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>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:14]1[N:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 44717667[2-Fluoro-4-(methylsulfanyl)phenyl]boronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 66673094HCID 66673094, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (0.16 g, 55%) was prepared as a light yellow solid from [2-fluoro-4-(methylthio)phenyl]boronic acid (prepared as in Example 161, Alternative synthesis, Step 2, 0.26 g, 1.4 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 0.25 g, 0.7 mmol), Na2CO3 (0.148 g, 1.4 mmol), Pd(PPh3)2Cl2 (49 mg, 0.07 mmol), water (1 mL) and DME (2 mL) in a manner similar to Example 21, Step 3. LRMS (APCI), m/z 419 (M+H).

Sources & evidence

ORD record
ord-572af1249c9c46c7a52a6a69ffb0aec3
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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