Methanol → HCID 67004450, compound

HRID 2095622Notes

Reaction equation

HRID 2095622 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([O:11][CH2:12][CH3:13])[C:3]=1[CH:4]=[O:5].[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[N:22][CH:23]=1)[NH:20][CH:19]=[CH:18]2.[OH-].[K+].[CH3:26]O>>[Br:14][C:15]1[CH:16]=[C:17]2[C:18]([CH:4]([C:3]3[C:6]([O:11][CH2:12][CH3:13])=[CH:7][CH:8]=[C:9]([F:10])[C:2]=3[Cl:1])[O:5][CH3:26])=[CH:19][NH:20][C:21]2=[N:22][CH:23]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 83881329HCID 83881329, compound

Product 1

HCID 67004450HCID 67004450, compound

Procedure

A solution of 2-Chloro-6-ethoxy-3-fluorobenzaldehyde (2.0 g, 9.8 mmol), 5-bromo-7-azaindole (1.8 g, 8.9 mmol) and KOH (797 mg, 14.2 mmol) in methanol (30 mL) was stirred for 48 h at room temperature. The reaction mixture was concentrated to dryness and diluted with saturated aq. ammonium chloride. The aq. layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were dried (Na2SO4) and concentrated to give a residue that was purified by column chromatography (5/95, methanol/DCM) to give the title compound as foamy solid. 1H NMR (CDCl3, 400 MHz): δ=1.35 (t, 3H, J=7.2 Hz), 3.43 (s, 3H), 4.0 (q, 1H, J=7.2 Hz), 4.07 (q, 1H, J=7.2 Hz), 6.39 (s, 1H), 6.81 (dd, 1H, J=4.0, 9.2 Hz), 7.01 (t, 1H, J=8.4 Hz), 8.06 (d, 1H, J=2.0 Hz), 8.29 (d, 1H, J=2.0 Hz), 9.49 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with saturated aq. ammonium chloride
  3. extractionThe aq. layer was extracted with ethyl acetate (2×30 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by column chromatography (5/95, methanol/DCM)

Sources & evidence

ORD record
ord-486b510887f54aa7b22b1c99b535ca54
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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