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Cesium carbonate → tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate

HRID 220340
ノート
印刷プレビュー

反応式

HRID 220340 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]2[N:27]=[CH:28][N:29]([CH3:30])[C:4]=2[CH:3]=1.[C:31](=[NH:44])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:26][O:25][C:18]1[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=1[CH2:16][N:8]([C:6]1[C:5]2[N:27]=[CH:28][N:29]([CH3:30])[C:4]=2[CH:3]=[C:2]([N:44]=[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:7]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]
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 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58180538tert-butyl 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate

生成物 1

HCID 58180611tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate
収率 89%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Anhydrous dioxane (4 mL) was added to a mixture of tert-butyl 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate (example 1B, 0.638 g, 1.474 mmol), benzophenone imine (0.297 mL, 1.769 mmol), Pd2(dba)3 (0.270 g, 0.295 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.256 g, 0.442 mmol), and cesium carbonate (0.672 g, 2.063 mmol). The reaction mixture was heated to 90° C. overnight. After cooling to rt, solvent was removed in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography using an Isco 40 g column eluting with 50-100% ethyl acetate/hexane to provide tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate (0.757 g, 89% yield) as a light yellow solid.

後処理

  1. temperatureAfter cooling to rt
  2. customsolvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography
  9. washeluting with 50-100% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-932d3f86af01455f9e11a0b025a57147
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202881B2

反応ノート

読み込み中…

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