Dimethylformamide → HCID 54112325, compound

HRID 1678140Notes

Reaction equation

HRID 1678140 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:10])[CH:8]=O.Cl.[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH2:14][C:13]1=[O:21]>ClCCl.N1C=CC=CC=1>[CH3:6][N:7]([CH:10]=[C:14]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:12][C:13]1=[O:21])[CH3:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 67373116HCID 67373116, compound

Product 1

HCID 54112325HCID 54112325, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Phosphorous oxychloride (1.93 mL, 3.17 mmol) is added slowly to a stirred solution of dimethylformamide (1.99 nmL) and dichloromethane (3 mL) cooled to 0-5° C. After 10 min, a solution of the above 1,3-dihydropyrrolo[2,3-b]pyridine-2-one hydrochloride (6-aza-1,3-dihydroindol-2-one) (790 mg, 4.63 mmol), pyridine (1.5 mL) and dichloromethane (5 mL) is added over 5 min and the reaction is stirred at room temperature for 18 hr. The solvents are removed to yield crude 3-dimethylaminomethylene-1,3-dihydropyrrolo[2,3-b]pyridin-2-one.

Workup

  1. customThe solvents are removed

Sources & evidence

ORD record
ord-b74a1292e8b34ee9856699efcb4a2750
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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