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Sodium Carbonate → 2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazole-4-carbonitrile

HRID 473977
ノート
印刷プレビュー

反応式

HRID 473977 の反応式
Br[C:2]1[S:6][C:5]([N:7]2[CH2:12][C@H:11]([CH3:13])[O:10][C@H:9]([CH3:14])[CH2:8]2)=[N:4][C:3]=1[C:15]#[N:16].[CH3:17][C:18]1[CH:23]=[C:22](B(O)O)[CH:21]=[C:20]([CH3:27])[N:19]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)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>[CH3:14][C@H:9]1[O:10][C@@H:11]([CH3:13])[CH2:12][N:7]([C:5]2[S:6][C:2]([C:22]3[CH:21]=[C:20]([CH3:27])[N:19]=[C:18]([CH3:17])[CH:23]=3)=[C:3]([C:15]#[N:16])[N:4]=2)[CH2:8]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

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 23546910(2,6-Dimethylpyridin-4-yl)boronic acidHCID 672167795-Bromo-2-(cis-2,6-dimethyl-morpholin-4-yl)-thiazole-4-carbonitrile

生成物 1

HCID 672165242-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazole-4-carbonitrile収率 85%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 19096565Water ethanol溶媒

反応条件

温度
130 °C

実験手順

A mixture of Intermediate 3 (20 g, 66.18 mmol), 2,6-dimethylpyridine-4-boronic acid, pinacol ester ([325142-95-8], 20 g, 85.79 mmol), tetrakis(triphenylphosphine)palladium (4.59 g, 3.97 mmol), 1,4-dioxane (120 mL), sodium carbonate (21.04 g, 198.55 mmol) in ethanol/water 1/1 (120 mL) was stirred and heated under nitrogen atmosphere at 130° C. for 6 h. The solvent was evaporated. The residue was taken up in DCM and washed twice with water. The organic layer was separated, dried with MgSO4 and evaporated. The residue was purified by column chromatography on silica gel (eluent gradient from 100% DCM to 98/2 DCM/MeOH). The desired fractions were collected and evaporated. The resulting residue was recrystallized from DIPE/CH3CN, yielding 18.5 g (85%) of Intermediate 4, after drying overnight under vacuum at 50° C.

後処理

  1. customThe solvent was evaporated
  2. washwashed twice with water
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (eluent gradient from 100% DCM to 98/2 DCM/MeOH)
  7. customThe desired fractions were collected
  8. customevaporated
  9. customThe resulting residue was recrystallized from DIPE/CH3CN

出典と根拠

ORDレコード
ord-f365e2cdb89142419e38feabb3eed020
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637510B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート