Aluminum(III) Chloride → HCID 69199550, compound

HRID 2377067Notes

Reaction equation

HRID 2377067 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=[CH:11][C:10]=3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Br)=[O:33])=[CH:30][CH:29]=1>ClCCl>[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([C:9]2[C:10]3[CH:11]=[N:12][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][C:15]=3[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:22][CH:21]=3)[CH:8]=2)=[O:33])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 122771214-Fluorobenzoyl bromideHCID 69199163HCID 69199163, compound

Product 1

HCID 69199550HCID 69199550, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 1-(4-fluorobenzyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (4.0 g, 13.4 mmol) in dichloromethane (60 mL) were added aluminum chloride (3.6 g, 26.8 mmol) and 4-fluorobenzoyl bromide (3.2 mL, 26.8 mmol). The resulting mixture was stirred for three days at ambient temperature. It was quenched with ice-water (100 mL), and extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with water (2×100 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with hexane:ethyl acetate (1:1) provided the title compound as a solid (2.2 g, 39% yield). 1H NMR (CDCl3) δ ppm 9.62 (s, 1H), 8.23 (s, 1H), 7.85-7.87 (m, 2H), 7.74 (s, 1H), 7.12-7.18 (m, 4H), 7.03-7.06 (m, 2H), 5.43 (s, 2H), 4.51 (q, 2H, J=7.2 Hz), 1.47 (t, 3H, J=7.2 Hz). LCMS (APCI, M+H+): 421.1.

Workup

  1. customIt was quenched with ice-water (100 mL)
  2. extractionextracted with dichloromethane (3×100 mL)
  3. washThe combined organic extracts were washed with water (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography
  7. washElution with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-61e7014dd14a4bfda9126d3a804fa15c
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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