Benzyl Bromide → HCID 178482272、化合物

HRID 2261191ノート

反応式

HRID 2261191 の反応式
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]2[NH:11][CH:12]=[CH:13][C:4]=12.C([O-])([O-])=O.[Na+].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([N:6]1[CH:7]=[C:8]([CH:9]=[O:10])[C:3]([NH:2][CH3:1])=[C:4]2[CH:13]=[CH:12][N:11]=[C:5]12)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 578391454-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

生成物 1

HCID 178482272HCID 178482272、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To solution of 4-methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.5 g, 2.86 mmol) in DMF is added Na2CO3 (900 mg, 8.6 mmol) and benzyl bromide (0.5 ml, 4.3 mmol). The reaction is stirred at room temperature for 12 hours. The reaction mixture is partitioned in 100 ml water and 100 ml ethyl acetate, extracted with ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by silica gel flash chromatography, eluted with 5% methanol in ethyl acetate to give the title compound as yellow solid. 1H NMR 400 MHz (DMSO-d6) δ 9.70 (s, 1H), 9.20 (q, 1H, J=5.2 Hz), 8.59 (s, 1H), 7.46 (m, 2H), 7.35 (m, 3H), 7.28 (d, 1H, J=2.8 Hz), 7.22 (d, 1H, J=2.4 Hz), 5.65 (s, 2H), 3.31 (d, 2H, J=2.4 Hz). MS m/z 266.2 (M+1).

後処理

  1. customThe reaction mixture is partitioned in 100 ml water
  2. extraction100 ml ethyl acetate, extracted with ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product is purified by silica gel flash chromatography
  6. washeluted with 5% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-3302c5f84c584bf38188a243160bb40c
出典データセット
uspto-grants-2010_12
特許番号
US07846923B2

反応ノート

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