Sodium Iodide → HCID 66604715, compound

HRID 2410791Notes

Reaction equation

HRID 2410791 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[I-].[Na+].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([F:35])[CH:28]=4)[CH:24]=[C:23]([C:36]([O:38][CH3:39])=[O:37])[C:19]=3[NH:20][C:21]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([F:35])[CH:28]=4)[CH:24]=[C:23]([C:36]([O:38][CH3:39])=[O:37])[C:19]=3[N:20]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=3)[C:21]=2[CH:22]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 66604957HCID 66604957, compound

Product 1

HCID 66604715HCID 66604715, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(Chloromethyl)-4-methoxybenzene (0.72 ml, 5.36 mmol) and sodium iodide (0.80 g, 5 4 mmol) were added to a stirred suspension of methyl 7-chloro-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.03 g, 2.68 mmol) and K2CO3 (1.11 g, 8.03 mmol) in DMF (10 ml) at RT. After 2 days this was diluted with EtOAc, washed with water (5×) and brine, and then dried with sodium sulfate. Removal of the solvent followed by radial silica gel chromatography (step gradient elution with hexane containing 0 to 50% DCM) afforded impure methyl 7-chloro-2-(3-fluoro-4-methoxyphenyl)-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (820 mg, 1.62 mmol, 61% yield) as a yellow solid that was used as such. MS (ESI) m/z 505.29 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.38 (2H, d, J=8.24 Hz), 7.92-7.97 (3H, m), 7.85 (1H, dd, J=8.55, 1.22 Hz), 7.46 (1H, s), 7.34 (1H, dd, J=8.24, 1.53 Hz), 7.06 (1H, t, J=8.70 Hz), 6.86 (2H, d, J=8.24 Hz), 6.75 (2H, d, J=8.55 Hz), 5.66 (2H, s), 3.95 (3H, s), 3.81 (3H, s), 3.73 (3H, s).

Workup

  1. washwashed with water (5×) and brine
  2. dry with materialdried with sodium sulfate
  3. customRemoval of the solvent
  4. washfollowed by radial silica gel chromatography (step gradient elution with hexane containing 0 to 50% DCM)

Sources & evidence

ORD record
ord-d2b5ad38bfd44b4facff9f1bceb2d9fd
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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