Phosphorus oxychloride → (+/-)-2-Chloro-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 2262846Notes

Reaction equation

HRID 2262846 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]3[CH2:23][C:13]4([C:21]5[C:16](=[N:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]4=[O:22])[CH2:12][C:7]=3[CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]3[CH2:23][C:13]4([C:21]5[C:16](=[N:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]4=[O:22])[CH2:12][C:7]=3[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517364HCID 178517364, compound

Product 1

HCID 59594283(+/-)-2-Chloro-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Procedure

A solution of (±)-2-hydroxy-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step B (3.00 g, 9.89 mmol) in POCl3 (30 mL) was stirred at 80° C. for 2 h, then concentrated to dryness under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (200 mL) and CH2Cl2 (500 mL). The aqueous layer was extracted further with CH2Cl2 (200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=322 (M+1).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (200 mL) and CH2Cl2 (500 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (200 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd8e63cc729c45f1817335aa1c223fda
Source dataset
uspto-grants-2010_12
Patent number
US07851464B2

Reaction notes

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