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

HRID 1914581노트

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HRID 1914581 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8312b86e2a9a40e09542164192c124d9
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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