Sodium Carbonate → 5-(2-Thiophen-3-yl-phenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 923278ノート

反応式

HRID 923278 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH2:11][CH2:10][CH2:9]1.[S:17]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[S:17]1[CH:21]=[CH:20][C:19]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:18]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

生成物 1

HCID 588271325-(2-Thiophen-3-yl-phenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

試薬・触媒・溶媒 2

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

実験手順

To a solution of 5-(2-bromophenyl)-5,6,7,8,-tetrahydroimidazo[1,5-a]pyridine (95 mg, 0.343 mmol) in DME (2 mL) is added thiophene-3-boronic acid (53 mg, 0.414 mmol), aqueous Na2CO3 (2M, 0.5 mL, 1.0 mmol), and Pd(PPh3)4 (20 mg). The reaction mixture is run under microwave irradiation at 120° C. for 20 min. The mixture is partitioned between EtOAc and brine. The organic layer is washed by brine, dried over Na2SO4 and concentrated to give an oil. The crude reaction mixture is subjected to flash chromatography eluting with acetone:hexane to yield the desired compound. MS (ESI) m/z 280 (M+H).

後処理

  1. customThe reaction mixture is run under microwave irradiation at 120° C. for 20 min
  2. customThe mixture is partitioned between EtOAc and brine
  3. washThe organic layer is washed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude reaction mixture
  8. washeluting with acetone

出典と根拠

ORDレコード
ord-74c24209bdcc4c10a0d74b38942a4429
出典データセット
uspto-grants-2016_03
特許番号
US09278969B2

反応ノート

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