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Diisopropylethylamine → 4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)benzene-sulfonic acid

HRID 349454
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HRID 349454 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[Na].C(N(C(C)C)CC)(C)C.[F:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]#[CH:43])=[CH:37][CH:36]=1>CN(C=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu]I>[F:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]#[C:43][C:2]2[CH:3]=[C:4]([C:8]3[N:9]=[N:10][N:11]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=4)[N:12]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:37][CH:36]=1
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8

반응물 4

HCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 105586681-Fluoro-4-prop-2-ynyl-benzeneHCID 865913364-[5-(3-Bromophenyl)tetrazol-2-ylmethyl]benzenesulfonic acid

생성물 1

HCID 865913354-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)benzene-sulfonic acid수율 8.26%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A suspension of 4-[5-(3-bromophenyl)tetrazol-2-ylmethyl]benzenesulfonic acid, sodium salt (0.50 g, 1.27 mmol) in DMF (3 mL) was treated with diisopropylethylamine (0.88 mL, 5.1 mmol), palladium tetrakis(triphenylphosphine) (“Pd(PPh3)4”, 0.29 g, 0.25 mmol), CuI (cat), and 1-fluoro-4-prop-2-ynyl-benzene (0.42 g, 3.1 mmol), and the mixture degassed with nitrogen. The reaction mixture was heated in the microwave for 15 minutes at 100° C., cooled to room temperature, poured into 1N HCl, extracted with EtOAc, washed with brine, dried over MgSO4, and evaporated onto silica gel. The mesh was purified on a 3.5×15 cm silica gel column eluted with ethyl acetate (“EtOAc”)-methanol (“MeOH”) 4:1 with 1% acetic acid (“AcOH”). Evaporation and trituration with ether afforded 0.052 g of orange solid (8.26% yield) NMR (DMSO-d6); 8.03–7.99 (m, 1H), 7.61–7.51 (m, 6H), 7.46–7.42 (dd, 1H), 7.36–7.33 (d, 2H), 7.19–7.15 (t, 2H), 5.98 (s, 2H), 3.90 (s, 2H)

후처리

  1. customthe mixture degassed with nitrogen
  2. temperaturecooled to room temperature
  3. additionpoured into 1N HCl
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated onto silica gel
  8. customThe mesh was purified on a 3.5×15 cm silica gel column
  9. washeluted with ethyl acetate (“EtOAc”)-methanol (“MeOH”) 4:1 with 1% acetic acid (“AcOH”)
  10. customEvaporation and trituration with ether

출처 및 근거

ORD 기록
ord-ebb5809445cd41b295913ee4168b6e8f
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179822B2

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