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(+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one → (+/-)-2a-Methyl-4-oxo-1,2,2a,3,4,5-hexahydropyrrolo[4,3,2-de]quinoline-6-carbonitrile

HRID 551096
Notes
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Reaction equation

HRID 551096 reaction equation
Br[C:2]1[C:11]2[NH:10][C:9](=[O:12])[CH2:8][C:7]3([CH3:15])[CH2:13][NH:14][C:5]([C:6]=23)=[CH:4][CH:3]=1.[Cu][C:17]#[N:18]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:7]12[CH2:13][NH:14][C:5]3=[C:6]1[C:11](=[C:2]([C:17]#[N:18])[CH:3]=[CH:4]3)[NH:10][C:9](=[O:12])[CH2:8]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 57955363(+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one2×HCID 178418546HCID 178418546, compound

Product 1

HCID 45118159(+/-)-2a-Methyl-4-oxo-1,2,2a,3,4,5-hexahydropyrrolo[4,3,2-de]quinoline-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of (±)-6-bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one (53 mg, 0.20 mmol, described in Intermediate 47), tetrakis(triphenylphosphine)palladium(0) (48 mg, 0.042 mmol), and copper(I) cyanide (27 mg, 0.30 mmol) in DMF (2 mL) was heated at 150° C. for 3 h. The cooled reaction mixture was quenched with aqueous NaHCO3 (10 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—60:40 to 0:100, to give the title compound in sufficient purity for use in the next step. MS: m/z=214 (M+1).

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched with aqueous NaHCO3 (10 mL)
  3. extractionextracted with EtOAc (30 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-c39be519cb6640d9b9a0833cabe59aef
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947677B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes