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

HRID 606143ノート

反応式

HRID 606143 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-63ae77092089449180833503888370ac
出典データセット
uspto-grants-2011_03
特許番号
US07915287B2

反応ノート

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