Lithium Chloride → HCID 21956523、化合物

HRID 2213098ノート

反応式

HRID 2213098 の反応式
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.FC(F)(F)S(O[C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:27]=1[O:34][CH3:35])(=O)=O.[Cl-].[Li+]>CN(C=O)C.C(OCC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][C:26]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:32]#[N:33]

参加物

8

反応物 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 166592584-Cyano-2-methoxyphenyl trifluoromethanesulfonate

生成物 1

HCID 21956523HCID 21956523、化合物

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 2-(tributylstannyl)pyridine (18 g of 80% pure, 39.2 mmol) and 4-cyano-2-methoxyphenyl trifluoromethanesulfonate (9.2 g, 32.7 mmol) were dissolved in DMF (65 mL) and treated with lithium chloride (1.39 g, 32.7 mmol) and Pd(PPh3)4 (1.9 g, 1.6 mmol), then degassed by bubbling argon through the solution for 15 min. The reaction mixture was heated to 100° C. while under an atmosphere of argon for 12 h. The cooled reaction mixture was diluted with diethyl ether (100 mL) and water (100 mL). The organic layer was separated and washed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1) to afford 3-methyoxy-4-pyridin-2-ylbenzonitrile.

後処理

  1. customdegassed
  2. customby bubbling argon through the solution for 15 min
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1)

出典と根拠

ORDレコード
ord-6f58c5203533400ebf11ac98e78b3bd2
出典データセット
uspto-grants-2006_09
特許番号
US07105533B2

反応ノート

読み込み中…