Benzyl Bromide → HCID 178482272, 화합물

HRID 2261191노트

반응식

HRID 2261191 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178482272HCID 178482272, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3302c5f84c584bf38188a243160bb40c
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846923B2

반응 노트

불러오는 중…