({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine → ({3-[(3-Butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine

HRID 1875164

반응식

HRID 1875164 반응식
Br[C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:19])=[C:12]([CH2:17][NH2:18])[CH:13]=[CH:14][C:15]=2[Cl:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br-].[CH2:21]([Zn+])[CH2:22][CH2:23][CH3:24]>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:19])=[C:12]([CH2:17][NH2:18])[CH:13]=[CH:14][C:15]=2[Cl:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH2:22][CH2:23][CH3:24]

참가 물질

6

반응물 2

HCID 68487182({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineHCID 178448256HCID 178448256, 화합물

생성물 1

HCID 68485437({3-[(3-Butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine수율 75%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of ({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (300 mg, 0.822 mmol) and tetrakis(triphenylphosphine)palladium(0) (950 mg, 0.822 mmol) in THF (4 ml) was added n-butyl zinc bromide (0.5 M solution in THF) (1.644 ml, 0.822 mmol) and the reaction mixture was heated at 60° C. for one hour. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give ({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (210 mg, 0.614 mmol, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.43 (s, 2H), 6.97 (s, 1H), 6.68 (s, 1H), 6.64 (s, 1H), 3.71 (s, 2H), 2.50 (t, 2H), 1.88 (br. s., 2H), 1.45 (quin, 2H), 1.14-1.29 (m, 2H), 0.82 (t, 3H).

후처리

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-b3fb5c0ec1c04ad8b8a17b7b1f0e60d6
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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