Sodium Chloride → 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 551888

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HRID 551888 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:21][C:22]1[CH:34]=[CH:33][C:25]2[O:26][C:27]([CH3:32])([CH3:31])[O:28][C:29](=[O:30])[C:24]=2[CH:23]=1.[BH4-].[Na+].[Na+].[Cl-]>C1(C)C=CC=CC=1.CO.C1COCC1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:21][C:22]3[CH:34]=[CH:33][C:25]4[O:26][C:27]([CH3:31])([CH3:32])[O:28][C:29](=[O:30])[C:24]=4[CH:23]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

9

반응물 4

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehydeHCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

생성물 1

HCID 114761686-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one수율 78%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 4-[(4-butylphenyl)ethynyl]benzaldehyde (5.43 g, 20.7 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one (4.00 g, 20.7 mmol) in toluene (60 mL) was heated at reflux for 3.5 hours with azeotropic removal of water. Then the mixture was cooled down to 0° C. and anhydrous THF (60 mL) and MeOH (60 1L) were added NaBH4 (1.65 g, 43.6 mmol) was added portionwise and the reaction mixture was stirred for 30 min at 0° C. and 45 min at rt. The reaction mixture was poured into a saturated solution of NaCl and extracted with Et2O. The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure to give the crude product. Precipitation from a mixture of EtOAc/MeOH gave 7.1 g (75%) of the title compound as a yellow powder. HPLC, Rt: 5.4 min (purity: 97.5%). 1H NMR (CDCl3) δ: 7.45 (d, J=8.3 Hz, 2H), 7.39 (d, J=8.3 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.15-7.06 (m, 3H), 6.80-6.70 (m, 2H), 4.20 (m, 2H), 4.04 (brs, 1H), 2.57 (t, J=7.7 Hz, 2H), 1.65 (s, 6H), 1.61-1.49 (m, 2H), 1.37-1.23 (m, 2H), 0.88 (t, J=7.3 Hz, 3H).

후처리

  1. additionwas added portionwise
  2. extractionextracted with Et2O
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customto give the crude product
  6. customPrecipitation
  7. additionfrom a mixture of EtOAc/MeOH

출처 및 근거

ORD 기록
ord-9930f1739ee4430cb3e5a3b083b12609
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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