Toluene → HCID 57576218, compound

HRID 604623Notes

Reaction equation

HRID 604623 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[I:18][C:19]1[C:20]([C:29](OCC)=[O:30])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.IC1C(C(OCCC(C)C)=O)=NC2C(C=1)=CC=CC=2.[BH4-].[Na+]>C1COCC1.CCO.O>[I:18][C:19]1[C:20]([CH2:29][OH:30])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

9

Reactant 5

HCID 1140TolueneHCID 4311764Sodium borohydrideHCID 21225700DiisobutylaluminumhydrideHCID 67057762HCID 67057762, compoundHCID 67057768HCID 67057768, compound

Product 1

HCID 57576218HCID 57576218, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisobutyl aluminum hydride in toluene (1M, 652 μL, 0.652 mmol) was added to a stirred solution of a 3:1 mixture of ethyl 3-iodoquinoline-2-carboxylate and 3-methylbutyl 3-iodoquinoline-2-carboxylate (100 mg, 0.297 mmol) in dry THF (3 mL) at 0° C. under N2. The reaction was stirred for 4 h at 0° C. The reaction was quenched with saturated NH4Cl (5 mL) and water (5 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. Sodium borohydride was added to a stirred solution of the crude product in EtOH (3 mL) and the reaction was stirred at room temperature for 20 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-50% EtOAc in hexanes gradient) to afford (3-iodoquinolin-2-yl)methanol, as a colorless solid. Rf=0.88 (50% EtOAc/hexanes). LCMS calc.=286.0; found=286.0 (M+1)+. 1H NMR (500 MHz, CDCl3): δ 8.56 (s, 1H); 8.03 (d, J=8.4 Hz, 1H); 7.74-7.71 (m, 1H); 7.70 (d, J=8.1 Hz, 1H); 7.54 (t, J=7.1 Hz, 1H); 4.90 (br s, 1H); 4.78 (s, 2H).

Workup

  1. customThe reaction was quenched with saturated NH4Cl (5 mL) and water (5 mL)
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. stirringthe reaction was stirred at room temperature for 20 min
  7. extractionextracted with EtOAc (3×20 mL)
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customto give the crude product
  12. customThis was purified by flash chromatography (Si, 12×160 mm, 0-50% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-2ac1f75beb404b4da54f222e8c4aad40
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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