Cesium fluoride → 6-Methyl-3-(2-pyrimidinyl)-2-pyridinecarbonitrile

HRID 1094758ノート

反応式

HRID 1094758 の反応式
CC1(C)COB([C:8]2[C:9]([C:15]#[N:16])=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=2)OC1.Br[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[F-].[Cs+]>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.[Cu]I.O1CCOCC1>[CH3:14][C:11]1[N:10]=[C:9]([C:15]#[N:16])[C:8]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:13][CH:12]=1

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 783452-BromopyrimidineHCID 593637323-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methyl-2-pyridinecarbonitrile

生成物 1

HCID 593637436-Methyl-3-(2-pyrimidinyl)-2-pyridinecarbonitrile

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

An alternative route to make D18 is: 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methyl-2-pyridinecarbonitrile D17 (50.6 mg) was dissolved 1,4-Dioxane (1 ml) under nitrogen in a vial, then 2-bromopyrimidine (42.0 mg, 0.264 mmol), CsF (67 mg, 0.441 mmol), Pd(Ph3P)4 (12 mg, 10.38 μmol) and CuI (7 mg, 0.037 mmol) were added in sequence. The vial was then capped and stirred at 65° C., after 1 hour the solvent was removed at reduced pressure and the residue partitioned between AcOEt (10 mls) and NaHCO3 (saturated solution, 10 ml). The phases were separated and the water was extracted with AcOEt (2×10 mls). The organic fraction were joined together, dried over Na2SO4 and evaporated at reduced pressure, obtaining an orange oily residue which was purified (Biotage, Snap 25 g silica gel column, AcOEt/Cy from pure Cy to 50:50 in 10 column volumes) to obtain the title compound D18 as pale yellow solid (27.6 mg).

後処理

  1. additionwere added in sequence
  2. customThe vial was then capped
  3. customwas removed at reduced pressure
  4. customthe residue partitioned between AcOEt (10 mls) and NaHCO3 (saturated solution, 10 ml)
  5. customThe phases were separated
  6. extractionthe water was extracted with AcOEt (2×10 mls)
  7. dry with materialdried over Na2SO4
  8. customevaporated at reduced pressure
  9. customobtaining an orange oily residue which
  10. customwas purified (Biotage, Snap 25 g silica gel column, AcOEt/Cy from pure Cy to 50:50 in 10 column volumes)

出典と根拠

ORDレコード
ord-811bd4e2c48b44559a7e26814be9fd4f
出典データセット
uspto-grants-2012_03
特許番号
US08133908B2

反応ノート

読み込み中…