Cesium fluoride → HCID 58975170, 화합물

HRID 737042노트

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HRID 737042 반응식
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8](=[O:36])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[C:40]1[CH:41]=[CH:42][C:43]([F:46])=[N:44][CH:45]=1.[F-].[Cs+]>CN(C=O)C.O.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>[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8](=[O:36])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:40]4[CH:45]=[N:44][C:43]([F:46])=[CH:42][CH:41]=4)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 27831685-Bromo-2-fluoropyridineHCID 58975028N-[(4-Fluorophenyl)methyl]-4-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl]sulfonyl]benzamide

생성물 1

HCID 58975170HCID 58975170, 화합물수율 70%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Combine N-(4-Fluoro-benzyl)-4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-sulfonyl]-benzamide (150 mg, 0.28 mmol), 5-Bromo-2-fluoro-pyridine (0.05 mL, 0.56 mmol), CsF (212 mg, 1.4 mmol) and Pd(Ph3P)4 (32 mg, 0.028 mmol) in 1.0 mL DMF and 0.100 mL of water. Evacuate the reaction vessel and place under an atmosphere of nitrogen. Heat the resulting reaction at 90 degrees 12 h. Load the reaction directly onto silica gel and purify by flash column chromatography (EtOAc/Hexanes) to yield 98 mg of white foam (70%) LRMS: MH+ 504.02.

후처리

  1. customEvacuate the reaction vessel and place under an atmosphere of nitrogen
  2. temperatureHeat
  3. customthe resulting reaction at 90 degrees 12 h
  4. customLoad the reaction directly onto silica gel
  5. custompurify by flash column chromatography (EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-730de51ea7c643a4b059b899f9d0f0bf
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595339B2

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