Sodium Carbonate → HCID 66673331, compound

HRID 423534Notes

Reaction equation

HRID 423534 reaction equation
[NH2:1][C:2](=[O:14])[CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:16]1[N:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:18][CH:17]=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>[NH2:1][C:2](=[O:14])[CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)=[CH:18][CH:17]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66673418{4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 66673331HCID 66673331, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Methylethyl 4-{[(6-{4-[(2-amino-2-oxoethyl)thio]phenyl}-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.139 g, 75%) was prepared as a light yellow solid from {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid (0.11 g, 0.50 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (Example 81, Step 1, 0.15 g, 0.42 mmol), 2M Na2CO3 (2 mL), Pd(PPh3)2Cl2 (30 mg, 0.04 mmol) and DME (2 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.36 (d, 1H, J=2.5 Hz), 7.90 (d, 2H, J=8.2 Hz), 7.65 (d, 1H, J=8.8 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.35-7.25 (m, 1H), 6.65 (bs, 1H), 5.41 (bs, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.23 (bs, 2H), 3.90 (d, 2H, J=6.3 Hz), 3.67 (s, 2H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 444 (M+H).

Sources & evidence

ORD record
ord-7cf90519c82e4f3fac37168a0a0689d2
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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