Dimethylformamide → HCID 66865502, compound

HRID 502187Notes

Reaction equation

HRID 502187 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](O)=[O:23])=[CH:18][CH:17]=1)#[N:2].C(Cl)Cl.[C:30](Cl)(=[O:34])[C:31](Cl)=O.[CH3:36][N:37](C=O)[CH3:38]>>[CH2:14]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:3]([C:1]#[N:2])=[C:4]1[C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]([N:37]2[CH2:38][CH2:31][CH:30]([OH:34])[CH2:36]2)=[O:23])=[CH:25][CH:26]=1)[CH3:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 59425469HCID 59425469, compound

Product 1

HCID 66865502HCID 66865502, compoundYield 79%

Procedure

[4-(3-Cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenoxy]-acetic acid (40 mg, 0.12 mmol) is suspended in CH2Cl2 (1.65 mmol) and DMF (2 μL). Oxalyl chloride (17 μL, 0.19 mmol) is added. This is stirred at room temperature for 30 minutes. The resulting solution is then pipetted into a stirring solution of S-3-hydroxypyrrolidine (150 μL) and CH2Cl2 (3.0 mL). The mixture is washed with aqueous HCl. The organic layer is dried and concentrated. Purification by silica gel chromatography (3/2 CH2Cl2/acetone) yields 1-ethyl-2-{4-[2-(3-hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-phenyl}-6-methoxy-1H-indole-3-carbonitrile (40 mg, 79%), compound 285 as a white solid.

Workup

  1. washThe mixture is washed with aqueous HCl
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (3/2 CH2Cl2/acetone)

Sources & evidence

ORD record
ord-a5097b37534c465b96c91a8e27c73d48
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…