Methyl iodide → HCID 10083868, compound

HRID 1813909Notes

Reaction equation

HRID 1813909 reaction equation
[H-].[Na+].C([N:11]1[CH2:28][CH2:27][CH:15]2[N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[CH:14]2[CH2:13][CH2:12]1)[CH:19]([OH:26])[CH2:18][CH2:17]3)(=O)C1C=CC=CC=1.I[CH3:30]>CN(C=O)C>[CH3:30][O:26][CH:19]1[C:20]2[C:25]3=[C:24]([CH:14]4[CH2:13][CH2:12][NH:11][CH2:28][CH2:27][CH:15]4[N:16]3[CH2:17][CH2:18]1)[CH:23]=[CH:22][CH:21]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22503724HCID 22503724, compound

Product 1

HCID 10083868HCID 10083868, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 0.50g, 1.2 mmol) was added to a solution of 10-benzoyl-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-4-ol (0.20 g, 0.58 mmol) in DMF (5.0 mL) at 0° C. under N2. After 30 min, iodomethane (0.040 mL, 0.64 mmol) was added. The reaction was quenched with saturated aqueous NH4Cl after 1 h and then allowed to warm to room temperature prior to extracting with EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with EtOAc/heptanes (2:1) to give 0.16 g (79%) of the title compound as a beige foam. 1H NMR (CDCl3) δ 7.46-7.30, 6.94, 4.51, 4.22-4.03, 4.01-3.79, 3.65-3.41, 3.29, 3.12, 3.04, 2.90, 2.82, 2.34, 2.08; IR (drift) 1631, 1493, 1477, 1459, 1422, 1370, 1359, 1324, 1292, 1267, 1098, 1085, 786, 748, 706 cm−1; HRMS (FAB) calcd for C23H24N2O2+H 361.1916, found 361.1913.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl after 1 h
  2. extractionto extracting with EtOAc
  3. washThe combined organic extracts were washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography with EtOAc/heptanes (2:1)

Sources & evidence

ORD record
ord-43dcb777440249c4b4095774fd6a6e2b
Source dataset
uspto-grants-2005_04
Patent number
US06875762B2

Reaction notes

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