Benzyl Bromide → HCID 86663064、化合物

HRID 2410853ノート

反応式

HRID 2410853 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:19]([O:21][CH3:22])=[O:20])[C:7]2[NH:8][C:9]3[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=3[C:15]=2[N:16]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CCOC(C)=O>[CH2:23]([N:8]1[C:9]2[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=2[C:15]2[N:16]=[C:4]([Br:3])[CH:5]=[C:6]([C:19]([O:21][CH3:22])=[O:20])[C:7]1=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86663065Methyl 2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate

生成物 1

HCID 86663064HCID 86663064、化合物収率 23.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (81 mg, 2 0 mmol) was added to a solution of methyl 2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (450 mg, 1.34 mmol) in THF (6 mL) in an ice bath. After 20 min this was removed from the bath and left stirring at RT for 0.5 h. Benzyl bromide (276 mg, 1.61 mmol) was added. After stirring at RT for 3 days, this was diluted with EtOAc, washed with water, brine, and dried over Na2SO4 Removal of the solvent followed by radial chromatography (elution with DCM) afforded methyl 5-benzyl-2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (130 mg, 0.31 mmol, 23% yield). MS (ESI) m/z 425.0 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.27 (1H, d, J=8.55 Hz), 7.59 (1H, s), 7.17-7.24 (3H, m), 6.97 (1H, dd, J=8.70, 1.98 Hz), 6.88-6.93 (2H, m), 6.84 (1H, d, J=1.83 Hz), 5.67 (2H, s), 3.86 (3H, s), 3.70 (3H, s).

後処理

  1. customAfter 20 min this was removed from the bath
  2. waitleft
  3. stirringAfter stirring at RT for 3 days
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4 Removal of the solvent
  6. washfollowed by radial chromatography (elution with DCM)

出典と根拠

ORDレコード
ord-ab58401c1d6c49e081013ac9bba637fd
出典データセット
uspto-grants-2014_08
特許番号
US08815840B2

反応ノート

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