Chloride → HCID 15661156、化合物

HRID 344962ノート

反応式

HRID 344962 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH3:16])=[C:7]([C:14]#[CH:15])[CH:8]=2)[O:3]1.Cl[C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=1.[Cl-]>C(N(CC)CC)C.[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>[CH2:26]([O:25][C:23](=[O:24])[C:22]1[CH:28]=[CH:29][C:19]([C:15]#[C:14][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][C:6]=2[CH3:16])[O:3][C:2]([CH3:17])([CH3:1])[CH2:11][C:10]3([CH3:12])[CH3:13])=[N:20][CH:21]=1)[CH3:27]

参加物

6

反応物 3

HCID 312ChlorideHCID 2799611Ethyl 6-chloronicotinate2 回HCID 156611392,2,4,4,7-Pentamethyl-6-ethynyl-chroman2 回

生成物 1

HCID 15661156HCID 15661156、化合物

試薬・触媒・溶媒 2

HCID 10122028Bis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒

反応条件

温度
60 °C

実験手順

A solution of 300 mg (1.316 mmol) of 2,2,4,4,7-pentamethyl-6-ethynyl-chroman (Compound 9) and 245.6 mg (1.3276 mmol) of ethyl 6-chloro-nicotinate (Compound 98) in 2 ml of triethylamine was placed in a pressure tube and a stream of nitrogen was bubbled through the solution for 15 min. The tube was then flushed with argon and a finely ground mixture 100 mg (0.1425 mmol) of bis (triphenylphosphine) palladium II) chloride and 50 mg (0.2625 mmol) of cuprous iodide was added to the solution. The pressure tube was then sealed and the reaction mixture heated at 60 degrees C. for 72 h. The mixture was cooled to room temperature and the triethylamine removed under vacuum. The residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane) to give the title compound as a yellow solid. PMR (CDCl3): & 1.37 (6H, s), 1.38 (6H, s), 1.44 (3H, t, J~7.2 Hz), 1.85 (2H, s), 2.49 (3H, s), 4.43 (2H, q, J~7.2 Hz), 6.70 (1H, s), 7.55-7.61 (2H, m), 8.28 (1H, dd, J~8.2 Hz, 2.1 Hz), 9.22 (1H, d, J~2.1 Hz). MS exact mass, m/e 377.1982 (calcd. for C24H27O3N, 377.1991).

後処理

  1. customa stream of nitrogen was bubbled through the solution for 15 min
  2. customThe tube was then flushed with argon
  3. customThe pressure tube was then sealed
  4. temperatureThe mixture was cooled to room temperature
  5. customthe triethylamine removed under vacuum
  6. customThe residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-eb5d5c3ab35a46958671ca0355fbeb62
出典データセット
uspto-grants-1991_10
特許番号
US05053523

反応ノート

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