2-Bromopropane → HCID 11755179, compound

HRID 1978951Notes

Reaction equation

HRID 1978951 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[CH:18]=[C:17]([I:19])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:30]([CH3:32])[CH3:31]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:20])[C:12]3[CH:18]=[C:17]([I:19])[S:16][C:13]=3[N:14]([CH:30]([CH3:32])[CH3:31])[CH:15]=2)=[O:9])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178522942HCID 178522942, compound

Product 1

HCID 11755179HCID 11755179, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno-[2,3-b]pyridine-5-carboxamide (Example No. 2) (2.00 g) in DMF (14 mL) are added K2CO3 (1.76 g) and 2-bromopropane (1.19 mL). The reaction is heated to 90° C. and stirred for 18 h. The reaction mixture is concentrated in vacuo. The resulting residue is partitioned between H2O (100 mL) and CH2Cl2 (200 mL). The aqueous layer is extracted with CH2Cl2 (3×150 mL). The combined organic layers are dried with MgSO4, filtered and concentrated in vacuo. The resulting yellow solid is purified via column chromatography (CH2Cl2, CH2Cl2:CH3OH; 99:1). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield a yellow solid. This material is recrystallized from ethanol then methanol to yield 0.808 g (39%) of the title compound as an off-white solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe resulting residue is partitioned between H2O (100 mL) and CH2Cl2 (200 mL)
  3. extractionThe aqueous layer is extracted with CH2Cl2 (3×150 mL)
  4. dry with materialThe combined organic layers are dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting yellow solid is purified via column chromatography (CH2Cl2, CH2Cl2:CH3OH; 99:1)
  8. concentrationconcentrated in vacuo
  9. customto yield a yellow solid
  10. customThis material is recrystallized from ethanol

Sources & evidence

ORD record
ord-ece6a8d8a5314c9488c4dd07519ecf09
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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