Hydrochloric Acid → 5-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid

HRID 2068648ノート

反応式

HRID 2068648 の反応式
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].O>[F:10][C:11]1[N:12]=[CH:13][C:14]([C:2]2[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=2)=[CH:15][CH:16]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 120399785-Bromothiophene-3-carboxylic acid

生成物 1

HCID 581101925-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid収率 83%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 5-bromo-thiophene-3-carboxylic acid (0.71 g, 4.4 mmol), 2-fluoropyridine-5-boronic acid (0.619 g, 4.4 mmol), caesium carbonate (2.9 g, 8.8 mmol), and palladium tetrakis(triphenylphosphine) (0.470 g, 0.44 mmol) in DME (40 mL), IMS 20 mL) and water (10 mL) was divided across three microwave vials and each was heated by microwave irradiation to 120° C. for 20 minutes. The batches were combined and concentrated and the residue was partitioned between saturated aqueous sodium carbonate and DCM. The aqueous phase was isolated and acidified using dilute HCl (pH 2) giving a precipitate which was collected by filtration to afford the title compound as a white solid (0.815 g). LCMS m/z 224.07 [M+H]+ R.T.=2.83 min (Analytical Method 8).

後処理

  1. concentrationconcentrated
  2. customthe residue was partitioned between saturated aqueous sodium carbonate and DCM
  3. customThe aqueous phase was isolated
  4. customgiving a precipitate which
  5. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-504463a5127247e2aa09e75cc7a60991
出典データセット
uspto-grants-2012_10
特許番号
US08299063B2

反応ノート

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