Sodium Carbonate → 5-(Pyrimidin-2-YL)thiophene-2-carbaldehyde

HRID 2416518ノート

反応式

HRID 2416518 の反応式
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[S:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>O.COCCOC.ClCCl.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>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[C:12]1[S:13][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27734305-Formyl-2-thiopheneboronic acid

生成物 1

HCID 226312225-(Pyrimidin-2-YL)thiophene-2-carbaldehyde収率 26%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of Na2CO3 (3.16 g) and 5-formyl-2-thiopheneboronic acid (2.4 g, 15.1 mmol) in water (15 mL) were added to a solution of 2-bromopyrimidine (2 g, 12.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (480 mg, 0.46 mmol) in DME (30 mL) and the mixture was heated to reflux for 24 hr. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded 620 mg (26%) of the title compound. MS 191 (M+H)+.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hr
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 1:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-2ccbb49f0c1a4c61aefa69f3b819d0d0
出典データセット
uspto-grants-2004_11
特許番号
US06825170B2

反応ノート

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