Triethylamine → HCID 71000688, 화합물

HRID 1023454노트

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HRID 1023454 반응식
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=1)#[CH:2].[F:13][C:14]1[CH:19]=[CH:18][C:17](I)=[C:16]([CH3:21])[CH:15]=1.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.[Cl-].[Cl-].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+2].[Cu]I.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=2)=[C:16]([CH3:21])[CH:15]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27745254-Fluoro-1-iodo-2-methylbenzeneHCID 86673609HCID 86673609, 화합물

생성물 1

HCID 71000688HCID 71000688, 화합물수율 19.8%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 84124Bis(triphenylphosphine)palladium chloride촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(4-Ethynyl-pyridin-2-yl)-urea (75 mg, 0.47 mmol), 4-fluoro-1-iodo-2-methyl-benzene (224 mg, 0.931 mmol), triethylamine (5.0 mL), palladium bis(triphenylphosphine)dichloride (16 mg, 0.023 mmol) and Copper (I) iodide (8.8 mg, 0.047 mmol) are mixed in DMF (1.8 mL). The reaction mixture is stirred for 16 hrs at room temperature before saturated NH4Cl solution (5 mL) is added along with water (25 mL). The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 5%) affords 25 mg of the desired product.

후처리

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by silica flash column chromatography

출처 및 근거

ORD 기록
ord-35fd92374f414824a16e4b2b340967da
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722709B2

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