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4-Bromo-2-methylpyridine → ethyl 4-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate

HRID 619628
ノート
印刷プレビュー

反応式

HRID 619628 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.C([Li])(C)(C)C.[CH3:14][C:15]1([CH3:46])[CH:24]=[C:23](OS(C(F)(F)F)(=O)=O)[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:33]#[C:34][C:35]3[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=3)[CH:21]=2)[S:16]1>C1COCC1.CCCCC.[Cl-].[Cl-].[Zn+2].[Pd].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>[CH3:8][C:4]1[N:5]=[CH:6][C:7]([C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:33]#[C:34][C:35]4[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=4)[CH:21]=3)[S:16][C:15]([CH3:14])([CH3:46])[CH:24]=2)=[CH:2][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 27628354-Bromo-2-methylpyridineHCID 10051511ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thio-chromen-6-ylethynyl)-benzoate2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 21846679ethyl 4-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate

試薬・触媒・溶媒 4

HCID 3007855Zincchloride
触媒
HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 8003Pentane溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 4-bromo-2-methylpyridine (220.0 mg, 1.28 mmol) in 2.0 mL of THF was cooled to -78° C. and tert-butyllithium (164.0 mg, 2.56 mmol, 1.5 ml of a 1.7M solution in pentane) was added to give a red-orange solution. After 30 minutes a solution of ZnCl2 (348.0 mg, 2.56 mmol) in 4.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature, stirred for 40 minutes, and transferred via cannula to a solution of ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)thiochromen-6-yl-ethynyl)-benzoate (Compound 224, 172.0 mg, 0.35 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.0 mg, 0.02 mmol) in 2.0 mL THF. This solution was heated to 50° C. for 2 hours, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. The solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 109.0 mg (72%) was isolated by column chromatography (5% EtOAc/hexanes) as a pale-yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.45 (1H, d, J=2.0 Hz), 8.00 (2H, d, J=8.5 Hz), 7.52 (2H, d, J=8.5 Hz), 7.49 (1H, dd, J=2.3, 8.1 Hz), 7.36 (2H, m), 7.20 (1H, d, J=8.1 Hz), 7.16 (1H, d, J=1.5 Hz), 5.86 (1H, s), 4.38 (2H, q, J=7.1 Hz), 2.63 (3H, s), 1.50 (6H, s), 1.40 (3H, t, J=7.1 Hz).

後処理

  1. customto give a red-orange solution
  2. temperatureThis solution was heated to 50° C. for 2 hours
  3. temperaturecooled to room temperature
  4. customthe reaction quenched by the addition of saturated aqueous NH4Cl
  5. extractionThe solution was extracted with EtOAc
  6. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  7. dry with materialbefore being dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-34671293d4ce42f7958174f4900a54b2
出典データセット
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05958954

反応ノート

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