Dimethylformamide → HCID 58010001, compound

HRID 1854463Notes

Reaction equation

HRID 1854463 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.O=S(Cl)Cl.[N-:36]=[N+:37]=[N-:38].[Na+].CN(C=O)C>C(Cl)Cl>[N:36]([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+:37]=[N-:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 58009987HCID 58009987, compound

Product 1

HCID 58010001HCID 58010001, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (0.63 g, 1.4 mmol) in DCM (10 mL) was treated with SOCl2 (0.115 mL, 1.58 mmol) and stirred for about 15 min at ambient temperature. The solvents were evaporated then sodium azide (0.280 g, 4.31 mmol) and DMF (5 mL) were added. The mixture was then stirred at ambient temperature overnight. The solvent was evaporated and the residue was partitioned between water (30 mL) and EtOAc (25 mL). The aqueous layer was washed with EtOAc (15 mL) then the combined organic solutions were dried over anhydrous MgSO4, filtered, and concentrated to give 2-(azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.58 g, 87%): LC/MS (Table 2, Method a) Rt=3.42 min; MS m/z: 464 (M+H)+.

Workup

  1. customThe solvents were evaporated
  2. stirringThe mixture was then stirred at ambient temperature overnight
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water (30 mL) and EtOAc (25 mL)
  5. washThe aqueous layer was washed with EtOAc (15 mL)
  6. dry with materialthe combined organic solutions were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-33ec8e48c7cd4180ab94e3b8d4df30f2
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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