Sodium Carbonate → HCID 24994033, compound

HRID 423507Notes

Reaction equation

HRID 423507 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)=[N:19][CH:20]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 59718568HCID 59718568, compound

Product 1

HCID 24994033HCID 24994033, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (0.39 g, 93%) was prepared as a white solid from [4-(methylsulfonyl)phenyl]boronic acid (0.23 g, 1.13 mmol), 1,1-dimethylethyl 4-{[(5-bromo-2-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.35 g, 0.94 mmol), 2M Na2CO3 (5 mL) and Pd(PPh3)4 (10 mg, 0.01 mmol) in DME (5 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CD3OD): δ 8.46 (d, 1H, J=2.7 Hz), 8.05-8.00 (m, 3H), 7.86 (d, 2H, J=8.5 Hz), 6.92 (d, 1H, J=8.6 Hz), 4.21 (d, 2H, J=6.3 Hz), 4.15-4.05 (m, 2H), 3.14 (s, 3H), 2.85-2.70 (m, 2H), 2.00-1.95 (m, 1H), 1.90-1.75 (m, 2H), 1.45 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 447 (M+H).

Sources & evidence

ORD record
ord-8942e26e738e41639ed4d083b1e54c2c
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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