Thionyl Chloride → (S)-2-(Chloromethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 656825Notes

Reaction equation

HRID 656825 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]3[CH2:24][C@:14]4([C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[NH:16][C:15]4=[O:23])[CH2:13][C:8]=3[CH:9]=2)[N:4]=1.S(Cl)([Cl:27])=O>ClCl>[Cl:27][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]3[CH2:24][C@:14]4([C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[NH:16][C:15]4=[O:23])[CH2:13][C:8]=3[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67016575(S)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 59594344(S)-2-(Chloromethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

To a stirred solution of (S)-2-(hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (203 mg, 0.64 mmol) in CH2 Cl2 (20 mL) was added thionyl chloride (761 mg, 6.40 mmol) and the resulting mixture was stirred at ambient temperature for 1 h, then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2 Cl2 (30 mL). The aqueous layer was extracted further with CH2 Cl2 (2×30 mL). The combined organic extracts were dried over Na2 SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=336 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2 Cl2 (30 mL)
  3. extractionThe aqueous layer was extracted further with CH2 Cl2 (2×30 mL)
  4. customThe combined organic extracts were dried over Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60cea02bd5384cf1b67e04961d0e63a0
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

Loading…