Phenol → HCID 57742823, 화합물

HRID 911877노트

반응식

HRID 911877 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[C:13]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:14]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23]Cl)[N:22]=2)=[N:15][CH:16]=1>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23][O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:22]=2)=[N:15][CH:16]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 57742594HCID 57742594, 화합물

생성물 1

HCID 57742823HCID 57742823, 화합물수율 20.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Phenol (0.0356 g, 0.378 mmol) was dissolved in 3 mL THF at ambient temperature. NaH (0.00907 g, 0.378 mmol) was added and the mixture stirred for 30 minutes at ambient temperature. Solid N-(5-Bromo-3-phenoxypyridin-2-yl)-4-(chloromethyl)thiazol-2-amine (0.030 g, 0.0756 mmol) (Example 322) was then added to the reaction and the mixture was stirred at ambient temperature overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2, washed with water, dried over Na2SO4, and concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (0.007 g, 20.4% yield) as the least polar of the two major products. 1H NMR (CDCl3) δ 5.07 (s, 2H), 6.88 (s, 1H), 6.96 (t, J=7.3 Hz, 1H), 7.01 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 7.14 (d, J=2.0 Hz, 1H), 7.23-7.31 (m, 3H), 7.43 (t, J=8.0 Hz, 2H), 8.14 (d, J=2.0 Hz, 1H), 8.76 (br s, 1H).

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. concentrationThe reaction was concentrated to dryness
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-156a254cd1e84ee5a314448ecbf12104
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022223B2

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