3-Ethoxyacryloyl chloride → (+/-)-(2E)-3-Ethoxy-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acrylamide

HRID 656837Notes

Reaction equation

HRID 656837 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[CH2:20]([O:22]/[CH:23]=[CH:24]/[C:25](Cl)=[O:26])[CH3:21]>ClCl.N1C=CC=CC=1>[CH2:20]([O:22]/[CH:23]=[CH:24]/[C:25]([NH:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2)=[O:26])[CH3:21]

Participants

5

Reactant 2

HCID 53255003-Ethoxyacryloyl chlorideHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Product 1

HCID 68675181(+/-)-(2E)-3-Ethoxy-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acrylamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24526ChlorineSolvent2×

Procedure

To a stirred suspension of (±)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (3.06 g, 12.2 mmol, described in Intermediate 4) in CH2 Cl2 (100 mL) and pyridine (40 mL) was added a solution of (E)-3-ethoxyacryloyl chloride [Tietze et al., Synthesis, 1993, 1079-1080](1.64 g, 12.2 mmol) in CH2 Cl2 (100 mL). The resulting mixture was stirred at ambient temperature for 1 h, then concentrated to dryness in vacuo. The residue was suspended in H2O (350 mL) with sonication and the solid was isolated by filtration and dried to give the title compound. MS: m/z=350 (M+1).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe residue was suspended in H2O (350 mL) with sonication
  3. customthe solid was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-59c4694491294a27827a2400ca5bdc9e
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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