Dimethylacetamide → 1-benzyl-3-chloro-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642431노트

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HRID 642431 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10](Cl)[N:11]=1)=[O:5])[CH3:2].C[C:26]([N:28](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:26]#[N:28])[N:11]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 2

HCID 31374DimethylacetamideHCID 866173511-Benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 684284231-benzyl-3-chloro-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
120 °C

실험 절차

A mixture of 1-benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (155 mg), Zn(CN)2 (30 mg), Zn dust (3.3 mg), Pd2(dba)3 (19.4 mg), dppf (23.5 mg) in DMA (1.5 mL) was heated to 120° C. for 90 min; then the mixture was partitioned between EtOAc and water, the organic phase was then washed with sat. NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated sequentially to give a residue, which was purified with column to give desired title compound (100 mg). 1H NMR (200 MHz, CDCl3): δ(ppm)=12.16 (s, 1H), 7.4-7.1 (m, 6H), 5.71 (s, 2H), 4.53 (q, 2H, J=7.1 Hz), 1.49 (t, 3H, J=7.1 Hz).

후처리

  1. customthen the mixture was partitioned between EtOAc and water
  2. washthe organic phase was then washed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated sequentially
  6. customto give a residue, which
  7. customwas purified with column

출처 및 근거

ORD 기록
ord-6d90022b6a224118a7bb782d379bd551
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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