Dimethylformamide → HCID 22638733, compound

HRID 1836663Notes

Reaction equation

HRID 1836663 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]3[CH2:17][CH:16]3[CH2:18][N:19]([CH3:21])[CH3:20])[CH:13]=2)[CH:8]=[CH:7]1.CN([CH:25]=[O:26])C>>[CH3:20][N:19]([CH2:18][CH:16]1[CH2:17][CH:15]1[C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH:25]=[O:26])=[CH:7][NH:6]2)=[CH:10][CH:11]=1)[CH3:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 22638707HCID 22638707, compound

Product 1

HCID 22638733HCID 22638733, compound

Procedure

Phosphorous oxychloride (0.23 g, 1.47 mmol) was added to dimethylformamide (2 mL) at room temperature with stirring. After 15 min, [2-(1H-indol-6-yl)-cyclopropylmethyl]-dimethyl-amine (0.35 g, 1.64 mmol) in DMF (3 mL) was added dropwise. After 20 h, the reaction was quenched with ice and 1 N NaOH. The solution was extracted with methylene chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 6-(2-dimethylaminomethyl-cyclopropyl)-1H-indole-3-carbaldehyde of an oil (0.25 g, 63%) that was used for the next reaction without purification. 1H NMR (CDCl3): δ9.84 (s, 1H), 8.14 (d, J=8.4 Hz, 1H), 7.97 (s, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.05 (s, 1H), 2.64 (s, 1H), 2.56 (s, 7H), 1.91 (m, 1H), 1.27 (m, 1H), 1.06 (m, 1H), and 0.92 (m, 1H).

Workup

  1. waitAfter 20 h
  2. customthe reaction was quenched with ice and 1 N NaOH
  3. extractionThe solution was extracted with methylene chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b596a38a14542d2837ec3cf345fd03c
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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