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

HRID 1443168노트

반응식

HRID 1443168 반응식
[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

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68679989HCID 68679989, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d8c20a56403b4806a2a9dd4b692483b4
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659297B2

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