Sodium Carbonate → 1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-({[4'-(1-pyrrolidinylcarbonyl)-4-biphenylyl]oxy}methyl)piperidine

HRID 423476

Reaction equation

HRID 423476 reaction equation
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]3[O:36][N:35]=[C:34]([CH:37]([CH3:39])[CH3:38])[N:33]=3)[CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[CH3:39][CH:37]([C:34]1[N:33]=[C:32]([N:29]2[CH2:28][CH2:27][CH:26]([CH2:25][O:24][C:21]3[CH:20]=[CH:19][C:18]([C:11]4[CH:12]=[CH:13][C:8]([C:6]([N:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:7])=[CH:9][CH:10]=4)=[CH:23][CH:22]=3)[CH2:31][CH2:30]2)[O:36][N:35]=1)[CH3:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2773571(4-(Pyrrolidine-1-carbonyl)phenyl)boronic acidHCID 666732104-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Product 1

HCID 591777881-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-({[4'-(1-pyrrolidinylcarbonyl)-4-biphenylyl]oxy}methyl)piperidineYield 4.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (4 mg, 4%) was prepared as a yellow solid from [4-(1-pyrrolidinylcarbonyl)phenyl]boronic acid (44 mg, 0.2 mmol), 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (prepared as in Example 24, Step 1, 76 mg, 0.2 mmol), Pd(PPh3)4 (50 mg, 0.04 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) in a manner similar to Example 1, Step 1, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.58 (s, 4H), 7.53 (d, 2H, J=8.8 Hz), 6.96 (d, 2H, J=8.8 Hz), 4.26-4.16 (m, 2H), 3.88 (d, 2H, J=6.4 Hz), 3.70 (t, 2H, J=7.0 Hz), 3.52 (t, 2H, J=6.6 Hz), 3.18-3.08 (m, 2H), 2.99-2.84 (m, 1H), 2.15-1.85 (m, 7H), 1.57-1.40 (m, 2H), 1.29 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 475 (M+H).

Sources & evidence

ORD record
ord-5c12ea7505a64a878cd9d269619a1545
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Linked notes

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