Dimethylformamide → HCID 66865502, compound

HRID 1009599Notes

Reaction equation

HRID 1009599 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-88a2c4fdcc084149b202aa7ebe06ea65
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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