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Triphenylphosphine → HCID 68899028, 화합물

HRID 735327
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HRID 735327 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9](O)[CH:10]=[CH2:11].I[C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH2:29].C(=O)([O-])O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)P(N(C)C)(N(C)C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:16]2[C:15](=[CH:14][CH:19]=[C:18]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:17]=2)[N:29]=1
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참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 57421915HCID 57421915, 화합물HCID 65416705HCID 65416705, 화합물

생성물 1

HCID 68899028HCID 68899028, 화합물수율 10.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매
HCID 12679Hexamethylphosphoramide용매

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온도
140 °C

실험 절차

1-(2,4-Difluorophenyl)prop-2-en-1-ol (Step 3, 260 mg, 1.41 mmol), [2-iodo-4-(phenylsulfonyl)phenyl]amine (Step 2, 359 mg, 1 mmol), palladium acetate (22 mg, 0.1 mmol), sodium hydrogencarbonate (162 mg, 3 mmol) and triphenylphosphine (26 mg, 0.1 mmol) were combined in hexamethylphosphoramide (5 mL) and heated to 140° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine (x5), dried over MgSO4 and evaporated. The residue was purified by preparative HPLC to give the title compound (39 mg). 1H NMR (500 MHz, CDCl3) δ 8.59 (1H, d), 8.32 (1H, d), 8.21-8.14 (2H, m), 8.10 (1H, dd, J=2.1, 8.9 Hz), 8.03-7.98 (3H, m), 7.61-7.52 (3H, m), 7.09-7.05 (1H, m), 6.99-6.94 (1H, m).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine (x5)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-3fdc9796593548c68e1eed9952289f3c
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592456B2

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