Potassium Carbonate → 10-[4-(1H-benzimidazol-2-yloxy)phenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 573285ノート

反応式

HRID 573285 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([O:13][C:14]3[NH:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:27]1[C:28]2[N:39]=[CH:38][CH:37]=[CH:36][C:29]=2[N:30]2[C:35]=1[CH2:34][CH2:33][CH2:32][CH2:31]2.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[NH:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:27]2[C:28]3[N:39]=[CH:38][CH:37]=[CH:36][C:29]=3[N:30]3[C:35]=2[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 6672788310-Bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizineHCID 866889652-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazole

生成物 1

HCID 6672806310-[4-(1H-benzimidazol-2-yloxy)phenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine収率 13.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
150 °C

実験手順

To a suspension of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzo[d]imidazole (320 mg), 10-bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizine (217 mg) and K2CO3 (119 mg) in DME (4 mL) and water (1 mL) was added Pd(PPh3)4 (100 mg). The mixture was heated at 150° C. for 40 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (43.4 mg).

後処理

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-14eb3b254427486893c5845be4f840de
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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