Water → 4-(4-Amino-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 2240249노트

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HRID 2240249 반응식
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C(F)(F)F)=[CH:14][C:13]=2[F:25])[N:4](S(C2C=CC(C)=CC=2)(=O)=O)[CH:3]=1.[CH3:36][N:37](C=O)C.O.[OH-].[Li+]>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.[Zn].[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:4][CH:3]=[C:2]([C:36]#[N:37])[C:10]=23)=[C:13]([F:25])[CH:14]=1

참가 물질

11

반응물 4

HCID 962Water2회HCID 3939Lithium HydroxideHCID 6228DimethylformamideHCID 59304989N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide

생성물 1

HCID 593049784-(4-Amino-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

시약·촉매·용매 6

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11192Zinc Acetate촉매HCID 23994Zinc촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

1.70 g (2.98 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide, 219 mg (1.19 mmol) of zinc acetate, 78 mg (1.19 mmol) of zinc dust, 189 mg (1.61 mmol) of zinc cyanide, 50.0 mg (0.09 mmol) of bis(diphenylphosphino)ferrocene and 27.3 mg (0.03 mmol) of tris(dibenzylideneacetone)dipalladium are initially charged. Under argon, a degassed mixture of 17 ml of DMF and 0.17 ml of water is added, and the mixture is heated at 100° C. for 20 hours. 10 ml of water, 8 ml of THF and 1.21 g (50.3 mmol) of lithium hydroxide are added to the crude mixture, which is then stirred at RT for 20 h. The mixture is concentrated a little and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: dichloromethane:methanol 25:1).

후처리

  1. additionis added
  2. concentrationThe mixture is concentrated a little and
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by chromatography on silica gel (mobile phase: dichloromethane:methanol 25:1)

출처 및 근거

ORD 기록
ord-d08bfc67665f4cc98d8f379cb6ef4955
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723347B2

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