Pyridine → Benzyl 3-bromo-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

HRID 1725924

반응식

HRID 1725924 반응식
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:18])[C:5]([Br:19])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[Br:19][C:5]1[C:6]([CH3:18])=[C:7]([C:2]([NH:1][S:27]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 68863679Benzyl 6-amino-3-bromo-2-methylbenzoate

생성물 1

HCID 68864112Benzyl 3-bromo-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoate수율 91.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of Example 126B (2.57 g, 7.13 mmol), 4-fluorobenzenesulfonyl chloride (1.92 g, 7.8 mmol) in dichloromethane (40 mL) was treated with pyridine (1.44 mL, 17.8 mmol), stirred for 48 hours at ambient temperature, washed with 1N HCl (2×30 mL). The organic solution was dried (MgSO4), filtered, and concentrated. The resulting solid was triturated twice with hexanes to provide the desired product (3.10 g, 91.2%). 1H NMR (DMSO-d6) δ 2.19 (s, 3H), 5.25 (s, 2H), 6.86 (d, 2H), 7.35-7.46 (m, 7H), 7.63 (d, 1H), 7.75 (m, 2H), 10.07 (s, 1H). MS (ESI(−)) m/e 476, 478 (M−H)−.

후처리

  1. washwashed with 1N HCl (2×30 mL)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated twice with hexanes

출처 및 근거

ORD 기록
ord-9cd44a0216e94b3bb6ccebd2baf84a9d
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491718B2

연결된 노트

불러오는 중…