Dichloromethane → Phenylmethyl 4-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoate

HRID 646686ノート

反応式

HRID 646686 の反応式
[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH2:13]([O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.ClCCl>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:26]2[CH:27]=[CH:28][C:23]([C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:22])=[CH:24][CH:25]=2)=[N:4][C:3]=1[C:9]([NH:11][CH3:12])=[O:10]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27732514-(Benzyloxycarbonyl)phenylboronic AcidHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamide

生成物 1

HCID 68650283Phenylmethyl 4-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoate収率 59.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a stirred mixture of 3-amino-6-bromo-N-methyl-2-pyrazinecarboxamide (0.577 g, 2.5 mmol), 4-benzyloxycarbonylphenylboronic acid (0.768 g, 3.0 mmol), triethylamine (1.01 g, 10 mmol) in 10 mL of DMF was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1), (20.4 mg, 0.025 mmol). The stirred mixture was warmed to 80-90° C. for 12 h and then concentrated on a rotary evaporator under reduced pressure. The residue was dissolved in 50 mL of EtOAc, washed with brine (30 mL). The organic layer was filtered through celite, and then dried over anhydrous sodium sulfate. Filtration, concentration and column chromatography on silica EtOAc) gave a solid (450 mg, 59.7% yield). 1H NMR (400 MHz; DMSO-d6): 8.91 (s, 1H); 8.84 (br s, 1H); 8.33 (d, 2H); 8.02 (d, 2H); 7.30-7.48 (m, 5H); 5.38 (s, 2H); 2.86 (s, 3M); MS (EI) for C20H15N4O3: 363 (MH+).

後処理

  1. concentrationconcentrated on a rotary evaporator under reduced pressure
  2. dissolutionThe residue was dissolved in 50 mL of EtOAc
  3. washwashed with brine (30 mL)
  4. filtrationThe organic layer was filtered through celite
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltration, concentration and column chromatography on silica EtOAc)

出典と根拠

ORDレコード
ord-d326b60a4af646aa98e463b402cc2bcb
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

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