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Iodine → HCID 57917305, 화합물

HRID 69206
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HRID 69206 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2COCC[Si](C)(C)C)=[CH:4][C:3]=1[CH:19]([C:21]1[N:25]2[N:26]=[C:27]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:28]=[CH:29][C:24]2=[N:23][CH:22]=1)O.FC1C(C(C2N3N=C(C4C=NN(C)C=4)C=CC3=NC=2)O)=CC2C(C=1)=NN(COCC[Si](C)(C)C)C=2.II.O[PH2]=O>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH2:19][C:21]1[N:25]2[N:26]=[C:27]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:28]=[CH:29][C:24]2=[N:23][CH:22]=1
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참가 물질

5

반응물 4

HCID 807IodineHCID 4124402Phosphinic AcidHCID 68640065(Rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1h-indazol-5-yl]-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanolHCID 68640136(Rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

생성물 1

HCID 57917305
HCID 57917305, 화합물

실험 절차

A mixture of (rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol and (rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol (Stage 164.3, 400 mg, 0.810 mmol), iodine (617 mg, 2.431 mmol) and H3PO2 (1.326 mL of a 50% aqueous solution, 12.16 mmol) were introduced in a microwave tube and the mixture was subjected to MW-irradiation at 150° C. for 5 min. The solvent was removed and the residue was taken up with 1 N HCl and washed with EtOAc three times. The aqueous layer was basified with NaOH pellets and extracted with EtOAc/MeOH (9:1) three times. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with DCM and MeOH to give the title compound as a light yellow solid (tR 0.90 min (conditions 2), MH+=348, 1H-NMR in DMSO-d6: 13.00 (s, 1H); 8.40 (s, 1H); 8.05 (m, 2H); 7.75 (d, 1H); 7.55 (m, 2H); 7.32 (d, 1H)).

후처리

  1. additionwere introduced in a microwave tube
  2. customThe solvent was removed
  3. washwashed with EtOAc three times
  4. extractionextracted with EtOAc/MeOH (9:1) three times
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed
  8. customThe residue was purified by MPLC with DCM and MeOH

출처 및 근거

ORD 기록
ord-b8544e40055c48a7803e3b63dbf8a8c1
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822468B2

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