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

HRID 349454
ノート
印刷プレビュー

反応式

HRID 349454 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-ebb5809445cd41b295913ee4168b6e8f
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07179822B2

反応ノート

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