Boron tribromide → 8-Bromo-1-[(1H-indazol-4-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalene-2,5-diol

HRID 1443168ノート

反応式

HRID 1443168 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:29]C)=[C:6]2[C:11]=1[CH:10]([NH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=1[CH:15]=[N:16][NH:17]3)[C:9]([C:23]([F:26])([F:25])[F:24])([OH:22])[CH2:8][C:7]2([CH3:28])[CH3:27].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[C:11]2[CH:10]([NH:12][C:13]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:14]=3[CH:15]=[N:16][NH:17]4)[C:9]([C:23]([F:24])([F:25])[F:26])([OH:22])[CH2:8][C:7]([CH3:27])([CH3:28])[C:6]=2[C:5]([OH:29])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68679989HCID 68679989、化合物

生成物 1

HCID 865999188-Bromo-1-[(1H-indazol-4-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalene-2,5-diol収率 84.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

21 mg (0.043 mmol) of 8-bromo-5-methoxy-1-[(1H-indazol-4-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-ol is mixed at room temperature with 0.4 ml of a 1 M BBr3 solution and stirred for 19 hours at room temperature. After the reaction mixture is mixed with ice, saturated sodium bicarbonate solution is added drop by drop, and it is diluted with ethyl acetate. The organic phases are washed neutral as usual, and the residue that remains after the solvent is spun in is chromatographed on silica gel (mobile solvent: methanol/dichloromethane). 17.1 mg (83.8%) of the desired compound (together with the Desbrom compound) is isolated.

後処理

  1. additionis added drop by drop, and it
  2. washThe organic phases are washed neutral as usual, and the residue that
  3. customin is chromatographed on silica gel (mobile solvent: methanol/dichloromethane)

出典と根拠

ORDレコード
ord-d8c20a56403b4806a2a9dd4b692483b4
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

反応ノート

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