N-Iodosuccinimide → HCID 22050193, 화합물

HRID 1832010노트

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HRID 1832010 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IN1C(=O)C[CH2:27][C:26]1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[C:26]#[CH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

생성물 1

HCID 22050193HCID 22050193, 화합물수율 118.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.83 g, 15.6 mmol) in anhydrous acetonitrile (55 mL) and N-iodosuccinimide (NIS, 3.86 g, 17.1 mmol) was heated at 65° C. under nitrogen for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel) using ethyl acetate/hexane (1:1 v:v). The appropriate fractions were collected according to ES MS (M+H 436) and washed with Na2SO3 to remove the color impurities. The fractions were concentrated under reduced pressure and dried in vacuo to afford the desired product (6.15 g, 90%) as a light yellow solid. 1H-NMR (CD3OD, 400 MHz) δ 7.73 (d, 1H, J=7.6 Hz), 7.47 (d, 2H, J=7.2 Hz), 7.39 (m, 4H), 7.08 (m, 3H), 6.39 (d, 1H, J=8.0 Hz), 5.29 (s, 2H), 5.19 (s, 2H); ES-HRMS m/z 436.0210 (M+H calculated for C19H16NO2FI requires 436.0196). Step 2. Preparation of 4-(benzyloxy)-1-(3-fluorobenzyl)-3-[(trimethylsilyl)ethynyl]pyridin-2(1H)-one

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel)
  3. customThe appropriate fractions were collected
  4. washwashed with Na2SO3
  5. customto remove the color impurities
  6. concentrationThe fractions were concentrated under reduced pressure
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-d1bfc3b6591c4209a8c3089cab7e3a3d
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067540B2

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