Sodium Carbonate → 6-Bromo-2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]thiazole

HRID 710093Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:21])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[F:20])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=3[F:20])[S:21][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Intermediate 33 (600 mg, 1.47 mmol) dissolved in DMF (7 ml) and added Na2CO3 (156 mg, 1.47 mmol). This mixture stirred at 110° C. for 17 h. Work up (EtOAc/H2O) afforded the crude. Crude was triturated with Petether and dried to obtain the titled compound (360 mg) as a white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.71-8.65 (m, 1H), 8.13 (d, J 1.9, 1H), 8.01 (d, J 8.7, 1H), 7.91-7.83 (m, 2H), 7.66 (dd, J 1.9, 8.7, 1H), 3.12 (s, 3H).

Workup

customafforded the crude
customCrude was triturated with Petether
customdried

Sources & evidence

ORD record: ord-75f988976c7346c7af5129294765661e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181214B2

Reaction notes

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