Thiophenol → 2-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 69463Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[O:7]1[C:11]2([CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:31][CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[C:27]([O:32]C)[CH:28]=5)[C:23]4=[O:34])=[CH:18][C:17]=3[F:35])[CH2:12]2)[O:10][CH2:9][CH2:8]1.C1(S)C=CC=CC=1.C(OCC)(=O)C>CN1C(=O)CCC1.O>[O:10]1[C:11]2([CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:31][CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[C:27]([OH:32])[CH:28]=5)[C:23]4=[O:34])=[CH:18][C:17]=3[F:35])[CH2:12]2)[O:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 200 °C

Procedure

Potassium carbonate (2.5 g) was added to a mixture of 2-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one (7.2 g) and thiophenol (2 g) in NMP (80.2 mL). Small portions of the reaction mixture were each heated for 20 min at 200° C. in a microwave. Then ethyl acetate and water were added to the mixture. The aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 384.41 (C21H21FN2O4); MS (ESI): 385 (M+H+).

Workup

extractionThe aqueous phase was extracted several times with ethyl acetate
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuum
customIn this way the product was obtained with molecular weight 384.41 (C21H21FN2O4)

Sources & evidence

ORD record: ord-e3782af8ed2e41cfb17a2742a7f7de26
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Reaction notes

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