Methyl iodide → HCID 44415960, compound

HRID 2264272Notes

Reaction equation

HRID 2264272 reaction equation
[CH:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23]C([O-])(C)C.[K+].CI>C1COCC1>[CH:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:23])[CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 44415977HCID 44415977, compound

Product 1

HCID 44415960HCID 44415960, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 13 (24 mg) was dissolved in THF (1 mL) and KOtBu (1 M in THF, 82 μL) was added. The mixture was stirred for 1 hr, followed by addition of methyl iodide (5.1 μL). The stirring was continued for additional 1 hr, then the solution was concentrated and the residue was purified by flash chromatography [silica gel, EtOAc] to afford 16 mg (82%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 8.65 (d, 1 H), 8.32 (d, 1 H), 8.13 (d, 1 H), 7.75 (s, 1 H), 7.15 (dd, 1 H), 6.71 (d, 1 H), 5.0 (m, 1 H), 3.90 (s, 3 H), 3.88 (m, 1 H), 2.10 (m, 2 H), 1.70 (m, 2 H), 1.60 (m, 2 H), 1.40 (m, 2 H), 1.20 (m, 2 H). MS (ESI) m/z: 308 (M+H)+.

Workup

  1. waitThe stirring was continued for additional 1 hr
  2. concentrationthe solution was concentrated
  3. customthe residue was purified by flash chromatography [silica gel, EtOAc]

Sources & evidence

ORD record
ord-d8feede6b3d04297a9391b117a816f20
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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