Sodium Carbonate → 1-Methylethyl 4-[({4'-[(methylsulfonyl)amino]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423489ノート

反応式

HRID 423489 の反応式
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].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][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([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:8][CH:7]=1)(=[O:4])=[O:3]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2773537(4-Methanesulfonamidophenyl)boronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

生成物 1

HCID 591778031-Methylethyl 4-[({4'-[(methylsulfonyl)amino]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate収率 25%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

The title compound (11 mg, 25%) was prepared as a tan solid from {4-[(methylsulfonyl)amino]phenyl}boronic acid (22 mg, 0.1 mmol), 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 36 mg, 0.1 mmol), Pd(PPh3)2Cl2 (25 mg, 0.04 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 7.55-7.45 (m, 4H), 7.30-7.20 (m, 2H), 6.95 (d, 2H, J=8.6 Hz), 6.38 (s, 1H), 4.99-4.83 (m, 1H), 3.84 (d, 2 H, J=6.4 Hz), 3.03 (s, 3H), 2.84-2.74 (m, 2H), 2.05-1.94 (m, 1H), 1.90-1.80 (m, 2H), 1.37-1.18 (m, 10H); LRMS (ESI), m/z 447 (M+H).

出典と根拠

ORDレコード
ord-1397930d79884d8189597199f61a1983
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

反応ノート

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