Benzyl Bromide → HCID 178482272, compound

HRID 2261191Notes

Reaction equation

HRID 2261191 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]2[NH:11][CH:12]=[CH:13][C:4]=12.C([O-])([O-])=O.[Na+].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([N:6]1[CH:7]=[C:8]([CH:9]=[O:10])[C:3]([NH:2][CH3:1])=[C:4]2[CH:13]=[CH:12][N:11]=[C:5]12)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 578391454-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 178482272HCID 178482272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 4-methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.5 g, 2.86 mmol) in DMF is added Na2CO3 (900 mg, 8.6 mmol) and benzyl bromide (0.5 ml, 4.3 mmol). The reaction is stirred at room temperature for 12 hours. The reaction mixture is partitioned in 100 ml water and 100 ml ethyl acetate, extracted with ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by silica gel flash chromatography, eluted with 5% methanol in ethyl acetate to give the title compound as yellow solid. 1H NMR 400 MHz (DMSO-d6) δ 9.70 (s, 1H), 9.20 (q, 1H, J=5.2 Hz), 8.59 (s, 1H), 7.46 (m, 2H), 7.35 (m, 3H), 7.28 (d, 1H, J=2.8 Hz), 7.22 (d, 1H, J=2.4 Hz), 5.65 (s, 2H), 3.31 (d, 2H, J=2.4 Hz). MS m/z 266.2 (M+1).

Workup

  1. customThe reaction mixture is partitioned in 100 ml water
  2. extraction100 ml ethyl acetate, extracted with ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product is purified by silica gel flash chromatography
  6. washeluted with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-3302c5f84c584bf38188a243160bb40c
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

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