Isopropyl iodide → HCID 59651915, compound

HRID 2042536Notes

Reaction equation

HRID 2042536 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[C:12](=[O:18])[NH:11][N:10]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH:26]([CH3:28])[CH3:27]>CN(C=O)C>[CH:26]([N:11]1[C:12](=[O:18])[C:13]2[CH:17]=[CH:16][S:15][C:14]=2[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:10]1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 12796524HCID 12796524, compound

Product 1

HCID 59651915HCID 59651915, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product from step 1 in 10 mL of DMF was added Cs2CO3 (2 eq. 1.95 g) and 2-iodopropane (1.2 eq., 360 uL). The reaction was heated to 80° C. for 2 h, and then filtered through celite, washed with MeOH:CH2Cl2 (95:5). The filtrate was concentrated and purified by silica gel flash chromatography (MeOH:CH2Cl2, 97:3) to afford 585 mg (65%) of the product: Mp 124-6° C.; MS m/z 301 (M+H).

Workup

  1. filtrationfiltered through celite
  2. washwashed with MeOH:CH2Cl2 (95:5)
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel flash chromatography (MeOH:CH2Cl2, 97:3)

Sources & evidence

ORD record
ord-14c00b20d72142849be11c16b736bad1
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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