Methyl iodide → HCID 25174277, compound

HRID 549448Notes

Reaction equation

HRID 549448 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8]([CH3:26])([CH3:25])[C@H:9]2[NH:12][C:13]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([Cl:24])=[CH:19][CH:18]=3)=[O:14])=[CH:5][CH:4]=1)#[N:2].[C:27](C1C=C2C(CC(C)(C)C2NC(C2NC3C(C=2)=CC(Cl)=CC=3)=O)=CC=1)#N.C([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[Cl:24][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:27])[C:15]([C:13]([NH:12][C@H:9]1[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:11]=3)[CH2:7][C:8]1([CH3:26])[CH3:25])=[O:14])=[CH:23]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25141102HCID 25141102, compoundHCID 57573872HCID 57573872, compound

Product 1

HCID 25174277HCID 25174277, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of Example 2 N-(6-cyano-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-5-chloro-1H-indole-2-carboxamide (30 mg, 0.083 mmol) and K2CO3 (34 mg, 2.48 mmol) in DMF (0.3 mL) was added methyl iodide (6 μL, 0.091 mmol) and the resulting mixture was stirred at rt for 16 h. Water (˜5 mL) was added dropwise followed by stirring for an additional 30 min. The precipitated solid was collected by vacuum filtration, rinsed with additional water (˜5 mL) and dried in vacuo to afford the title product as a white solid (26 mg). HPLC Ret. time: 3.79 min. LCMS MH+ (m/z) 378.30. 1H NMR: (DMSO-d6, 400 MHz): 8.72 (d, 1H), 7.71 (s, 1H), 7.68 (d, 1H), 7.65 (s, 1H), 7.58 (d, 1 H), 7.44 (d, 1 H), 7.26 (dd, 1 H), 7.18 (s, 1H), 5.34 (d, 1H), 4.00 (s, 3H), 2.52-2.48 (m, 2 H), 1.21 (s, 3H), 0.95 (s, 3H).

Workup

  1. stirringby stirring for an additional 30 min
  2. filtrationThe precipitated solid was collected by vacuum filtration
  3. washrinsed with additional water (˜5 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-88764cb0f6304cea83ad85fc40e54849
Source dataset
uspto-grants-2011_05
Patent number
US07943658B2

Reaction notes

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