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

HRID 1623071Notes

Reaction equation

HRID 1623071 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]3[CH2:32][C@:14]4([C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]4=[O:31])[CH2:13][C:8]=3[CH:9]=2)[N:4]=1.S(Cl)([Cl:35])=O>C(Cl)Cl>[Cl:35][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]3[CH2:32][C@:14]4([C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[N:16]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]4=[O:31])[CH2:13][C:8]=3[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67016509(S)-2-(Hydroxymethyl)-1'-{[2-(trimethylsilyl)ethoxy]methyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 59594346(S)-2-(Chloromethyl)-1'-{[2-(trimethylsilyl)ethoxy]methyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-2-(hydroxymethyl)-1′-{[2-(trimethylsilyl)ethoxy]methyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (1.44 g, 3.22 mmol) in CH2Cl2 (10 mL) was added thionyl chloride (7.66 g, 64.3 mmol) and the resulting mixture was stirred at ambient temperature for 30 min, then concentrated in vacuo. The residue was concentrated in vacuo from toluene (2×10 mL) to give the title compound in sufficient purity for use in the next step. MS: m/z=466 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationThe residue was concentrated in vacuo from toluene (2×10 mL)

Sources & evidence

ORD record
ord-22d1d0087d0a46c99aa370c53a79537f
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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