1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-1,4-dimethyl-6-hexadecyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

HRID 60400노트

반응식

HRID 60400 반응식
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:9][C:10]([CH3:11])=[C:5]2[CH2:4][CH2:3]1.[Br:28]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)Cl>[Br:28][C:9]1[C:10]([CH3:11])=[C:5]2[CH2:4][CH2:3][N:2]([CH3:1])[C:6]2=[N:7][C:8]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

4

반응물 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 716778991,4-Dimethyl-6-hexadecyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 716780615-Bromo-1,4-dimethyl-6-hexadecyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

To a solution of 278 mg (0.75 mmol) of 1,4-dimethyl-6-hexadecyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 4 mL of chloroform was added 108 mg (0.38 mmol) of 1,3-dibromo-5,5-dimethylhydantoin in portions at 0° C. The reaction mixture was stirred at 0° C. for 30 min. The reaction was quenched by the addition of 5 mL of sat aq NaHCO3. The mixture was extracted with chloroform and the combined organic layer was washed with brine and dried over MgSO4. The concentrated residue was purified by flash chromatography on a silica gel column (20 1.7 cm). Elution with 100:1 hexanes/ethyl acetate gave the product as a white solid: yield 331 mg (98%); nip 49-50° C.; silica gel TLC Rf 0.78 (8:1:1 hexanes/ethyl acetate/methanol); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=7.2 Hz), 1.25-1.31 (m, 28H), 1.66 (quint, 2H, J=7.6 Hz), 2.08 (s, 3H), 2.55 (t, 2H, j=8.0 Hz), 2.80 (t, 2H, J=8.4 Hz), 2.90 (s, 3H), 3.38 (t, 2H, J=8.0 Hz) and 6.13 (s, 1H); 13C NMR (CDCl3), δ 14.1, 19.5, 22.7, 25.2, 28.7, 29.4, 29.57, 29.61, 29.65, 29.68, 29.71, 29.71, 29.71, 29.71, 29.71, 29.71, 31.9, 33.0, 38.1, 52.4, 110.9, 120.3, 141.1, 156.8 and 161.8; mass spectrum, m/z 451.3 and 453.2 (M+H)+ (theoretical 451.3 and 453.3); mass spectrum (APCI), m/z 451.2680 and 453.2697 (M+H)+ (C25H44N2Br requires 451.2688 and 453.2667).

후처리

  1. customThe reaction was quenched by the addition of 5 mL of sat aq NaHCO3
  2. extractionThe mixture was extracted with chloroform
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe concentrated residue was purified by flash chromatography on a silica gel column (20 1.7 cm)
  6. washElution with 100:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-85273a2637a7473badb926db5fa16366
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440967B2

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