Benzyl Bromide → HCID 118159794, compound

HRID 628407Notes

Reaction equation

HRID 628407 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][N:15]=3)[NH:10][C:5]2=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([N:10]1[C:5]2[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=[C:9]1[C:11]1[O:12][CH:13]=[CH:14][N:15]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 118159878HCID 118159878, compound

Product 1

HCID 118159794HCID 118159794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred mixture of 5-chloro-2-(1,3-oxazol-2-yl)-1H-pyrrolo[3,2-b]pyridine (0.39 g, 1.8 mmol, from Step 2) in DMF (8 mL) was added Cs2CO3 (1.7 g, 5.3 mmol) and benzyl bromide (0.21 mL, 1.8 mmol, Aldrich). After stirring overnight, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with an additional two portions of EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The resulting light yellow crystalline solid was used directly in Step 4. LCMS (M+H)+: 310.1/312.1.

Workup

  1. stirringAfter stirring overnight
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with an additional two portions of EtOAc
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0669b2f3ad1d4a1e8b499cd6ef8a0b45
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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