Tetrabutylammonium Fluoride → 3-(2-Hydroxyethyl)-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one

HRID 627802Notes

Reaction equation

HRID 627802 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:28]=2)[N:23]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:22]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:40])[CH3:41])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:28]=2)[N:23]([C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 711436503-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one

Product 1

HCID 711436113-(2-Hydroxyethyl)-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one (123 mg, 0.1476 mmol) dissolved in THF (2 mL) under N2. TBAF in THF (442.8 μL of 1.0 M, 0.4428 mmol) in THF added and the mixture stirred for 90 mins. Reaction mixture partitioned between DCM and brine. Aqueous phase extracted with DCM and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petrol gradient). Title compound obtained as a yellow film, (87 mg, 82%), taken on directly to deprotection reaction; MS (ES+) 719.0.

Workup

  1. customReaction mixture
  2. custompartitioned between DCM and brine
  3. extractionAqueous phase extracted with DCM
  4. customcombined organics dried
  5. concentrationconcentrated
  6. customResidue purified by chromatography (silica, 0-100% EtOAc-petrol gradient)

Sources & evidence

ORD record
ord-04d32ebf7ab342cf8a4356dcc2adb40f
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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