Sodium Carbonate → tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79580ノート

反応式

HRID 79580 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:18]1[C:19]([N:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[C:20]2[CH:26]=[CH:25][NH:24][C:21]2=[N:22][CH:23]=1>O1CCOCC1.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[C:19]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 68760498tert-butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 68760091tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate収率 66.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

4-Fluorophenylboronic acid (44.0 mg, 0.315 mmol), PS-palladium tetrakis (119 mg, 0.0131 mmol) and 2N sodium carbonate (262 μL, 0.525 mmol) were added to tert-butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (100 mg, 0.262 mmol, see Example 1) in dioxane (1 mL, degassed with Ar). The reaction was heated to 150° C. for 1 hour under microwave irradiation. The reaction was then cooled down and filtered. The filtrate was diluted with DCM and dried with MgSO4. After concentration, the residue was purified by chromatography (SP4, 25+M, water/ACN 90/10→10/90, 20CV) to yield tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (69 mg, 66.4% yield) as a solid.

後処理

  1. temperatureThe reaction was then cooled down
  2. filtrationfiltered
  3. additionThe filtrate was diluted with DCM
  4. dry with materialdried with MgSO4
  5. concentrationAfter concentration
  6. customthe residue was purified by chromatography (SP4, 25+M, water/ACN 90/10→10/90, 20CV)

出典と根拠

ORDレコード
ord-f0fd674d11c84d37b157ef92245d153d
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

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