Methyl iodide → HCID 87097575, compound

HRID 2174947Notes

Reaction equation

HRID 2174947 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[N:14]=[CH:13][C:12]4[N:18]([CH3:35])[C:19](=[N:32][C:33]#[N:34])[N:20]([C:21]5[CH:26]=[CH:25][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=5)[C:11]=4[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:36]([F:39])([F:38])[F:37].[CH3:40]C(C)([O-])C.[K+].CI>C1COCC1>[C:30]([C:27]([C:24]1[CH:23]=[CH:22][C:21]([N:20]2[C:11]3[C:10]4[CH:9]=[C:8]([C:5]5[CH:6]=[N:7][C:2]([NH:1][CH3:40])=[C:3]([C:36]([F:38])([F:37])[F:39])[CH:4]=5)[CH:17]=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:18]([CH3:35])[C:19]2=[N:32][C:33]#[N:34])=[CH:26][CH:25]=1)([CH3:28])[CH3:29])#[N:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 87097719HCID 87097719, compound

Product 1

HCID 87097575HCID 87097575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of Example 6 (0.014 mmol) in dry THF was added potassium-t-butoxide (0.157 mmol) at 0° C. Reaction mixture was stirred further for 15 minutes, followed by addition of methyl iodide (0.125 mmol). Reaction mixture was warmed to RT and stirred overnight. Solvent was removed and diluted with EtOAc. Organic layer was washed with water, dried over anhydrous Na2SO4 and solvent was removed. Crude product was further purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.16-8.11 (m, 2H), 8.00-7.91 (m, 1H), 7.89 (s, 3H), 7.76 (brs, 1H), 6.87 (d, J=1.8 Hz, 1H), 6.79 (q, J=4.5 Hz, 1H), 3.92 (s, 3H), 2.89 (d, J=4.2 Hz, 3H), 1.82 (s, 6H); MS (m/z): 541(M+1)+.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. stirringstirred overnight
  4. customSolvent was removed
  5. additiondiluted with EtOAc
  6. washOrganic layer was washed with water
  7. dry with materialdried over anhydrous Na2SO4 and solvent
  8. customwas removed
  9. customCrude product was further purified (silica gel column, MeOH/CHCl3 as eluent)

Sources & evidence

ORD record
ord-0bc3215e64ba4e788645a2a1f10f177b
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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