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Dichloromethane → HCID 58010001, compound

HRID 1628056
Notes
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Reaction equation

HRID 1628056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21]O)[N:20]=[C:15]2[CH:14]=1.C(Cl)Cl.S(Cl)(Cl)=O.[N-:39]=[N+:40]=[N-:41].[Na+]>O>[N:39]([CH2:21][C:19]1[N:20]=[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=1)=[N+:40]=[N-:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 58009987HCID 58009987, compound

Product 1

HCID 58010001HCID 58010001, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (4.00 g, 9.12 mmol, Preparation #F.1), DCM (90 mL) and thionyl chloride (0.732 mL, 10.0 mmol). The mixture was stirred at rt for about 40 min and concentrated under reduced pressure. The residue was dissolved in DMF (90 mL) and treated with NaN3 (1.48 g, 22.8 mmol). The mixture was stirred overnight at rt. The solution was diluted with water (150 mL). The suspension was extracted with EtOAc (3×125 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 2-(azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (4.23 g, 100%): LC/MS (Table 2, Method b) Rt=3.16 min; MS m/z 464 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF (90 mL)
  3. stirringThe mixture was stirred overnight at rt
  4. extractionThe suspension was extracted with EtOAc (3×125 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e5a3d837b54418b80c1b2efed896284
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785639B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes