Sodium Carbonate → HCID 59177823, compound

HRID 423481Notes

Reaction equation

HRID 423481 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:16]1[CH: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>[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:16]2[CH:17]=[CH:18][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:20][CH:21]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 35037674-(Dimethylcarbamoyl)phenylboronic AcidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 59177823HCID 59177823, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (29 mg, 27%) was prepared as a white solid from {4-[(dimethylamino)carbonyl]phenyl}boronic acid (39 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 7.63-7.42 (m, 6H), 6.96 (d, 2H, J=8.8 Hz), 4.98-4.81 (m, 1H), 4.20 (bs, 2H), 3.84 (d, 2H, J=6.4 Hz), 3.13 (s, 3H), 3.04 (s, 3H), 2.84-2.74 (m, 2H), 2.08-1.92 (m, 1H), 1.90-1.80 (m, 2H), 1.37-1.14 (m, 8H); LRMS (ESI), m/z 425 (M+H).

Sources & evidence

ORD record
ord-3274fe876cea44f4ba4a9f2058c8b63e
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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