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Water → 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-5-hydroxy-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)pyridin-4(1H)-one

HRID 571073
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HRID 571073 반응식
[Cl:1][C:2]1[C:3]([C:11]2[CH:12]=[C:13]([N:17]3[CH:22]=[C:21]([O:23]CC4C=CC(OC)=CC=4)[C:20](=[O:33])[CH:19]=[C:18]3[CH:34]=[O:35])[CH:14]=[CH:15][CH:16]=2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:36]1([C:42]#[C:43][Mg]Br)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>C1COCC1>[Cl:1][C:2]1[C:3]([C:11]2[CH:12]=[C:13]([N:17]3[CH:22]=[C:21]([OH:23])[C:20](=[O:33])[CH:19]=[C:18]3[CH:34]([OH:35])[C:43]#[C:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:14]=[CH:15][CH:16]=2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 866802761-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-5-(4-methoxy-benzyloxy)-4-oxo-1,4-dihydro-pyridine-2-carbaldehydeHCID 178419644HCID 178419644, 화합물

생성물 1

HCID 699316101-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-5-hydroxy-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)pyridin-4(1H)-one

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 0.05 g (0.01 mmol) 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-5-(4-methoxy-benzyloxy)-4-oxo-1,4-dihydro-pyridine-2-carbaldehyde in 3 mL THF at −40° C. was added 1 mL phenylethynylmagnesium bromide (1.0 M in THF). The reaction mixture was stirred at −40° C. for 30 min before 1 mL of water was added. The reaction was gravity filtered through an Isolute HM-N tube, which was rinsed with 4 mL EtOAc and the combined organics were concentrated. The resulting residue was dissolved in 1 mL TFA and allowed to stand at room temperature for 5 min before being concentrated. Purification by automated mass-guided HPLC afforded 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-5-hydroxy-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)pyridin-4(1H)-one. Compound exhibits equilibrating rotational isomerism in solution. Reported NMR data correlates to the major rotational isomer. 1H NMR (500 MHz, CD3OD, 0° C.): δ 8.26 (s, 1H); 7.96 (s, 1H); 7.89-7.78 (m, 3H); 7.71 (t, J=8.59 Hz, 1H); 7.50 (d, J=3.49 Hz, 1H); 7.41-7.36 (m, 5H); 6.34 (d, J=3.46 Hz, 1H); 5.45 (s, 1H). HRMS (FT/ICR) Calc (M+H)+ 468.1109. Found 468.1109.

후처리

  1. additionwas added
  2. filtrationfiltered through an Isolute HM-N tube, which
  3. washwas rinsed with 4 mL EtOAc
  4. concentrationthe combined organics were concentrated
  5. dissolutionThe resulting residue was dissolved in 1 mL TFA
  6. concentrationbefore being concentrated
  7. customPurification by automated mass-guided HPLC

출처 및 근거

ORD 기록
ord-e30179e10e1d4f32b9408698e11f520e
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09024032B2

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