Hydrogen Bromide → 5-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamide

HRID 606143노트

반응식

HRID 606143 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([F:26])[CH:19]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].Br>CC(O)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:26])[CH:19]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 597811305-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide

생성물 1

HCID 597811355-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamide수율 91%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

This process was repeated with 5-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide (2.78 g, 6.7 mmol), HOAc (7 ml), and hydrobromic acid (48%, 23 ml, 424 mmol). Both reactions were combined, and the pH of the aqueous phase was raised to above 12, and then washed with DCM. Then, the pH of the aqueous phase was lowered to 6 with concentrated HCl, and the aqueous phase was extracted with 10:1 DCM/MeOH). The organic extracts were combined and concentrated to afford the desired 5-bromo-2-(3-fluoro-4-hydroxyphenylamino)-N-phenylnicotinamide (2.45 g, 6.10 mmol, 70% purity, 52% yield). MS (ESI pos. ion) m/z: 402 (MH+, 79Br), 404 (MH+, 81Br). Calc'd exact mass for C18H13BrFN3O2: 401 (79Br), 403 (81Br).

후처리

  1. temperaturethe pH of the aqueous phase was raised to above 12
  2. washwashed with DCM
  3. extractionthe aqueous phase was extracted with 10:1 DCM/MeOH)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-63ae77092089449180833503888370ac
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915287B2

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