N-bromobutanimide → HCID 90466000, compound

HRID 928550Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[C:15]3[O:16][CH2:17][CH:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:13]4[C:14]=3[C:10]([CH:11]=[N:12]4)=[CH:9][CH:8]=2)=[C:5]([CH3:25])[O:4][N:3]=1.[Br:26]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[Br:26][C:9]1[CH:8]=[C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:25])[C:15]2[O:16][CH2:17][CH:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:13]3[C:14]=2[C:10]=1[CH:11]=[N:12]3

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 9-(3,5-dimethylisoxazol-4-yl)-3-phenyl-2,3-dihydro[1,4]oxazino[2,3,4-hi]indazole (0.011 g, 0.033 mmol) in acetonitrile (0.4 mL) at 0° C. was treated with N-bromosuccinimide (8.3 mg, 0.047 mmol) and stirred at 0° C. for 30 min. The reaction mixture was diluted with EtOAc (20 mL) and washed with saturated sodium bicarbonate solution (20 mL), dried over sodium sulfate, filtered, and concentrated to a colorless residue. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 30 mL/min) gave desired product (9 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 8.11 (s, 1H), 7.40-7.32 (m, 3H), 7.28 (s, 1H), 7.16-7.05 (m, 2H), 5.99-5.89 (m, 1H), 4.81 (dd, J=11.7, 3.4 Hz, 1H), 4.71 (dd, J=11.6, 4.8 Hz, 1H), 2.32 (s, 3H), 2.16 (s, 3H); LCMS calculated for C20H17BrN3O2 (M+H)+: m/z=410.0, 412.0. found: 410.0, 412.0.

Workup

washwashed with saturated sodium bicarbonate solution (20 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated to a colorless residue
customPurification via preparative LCMS (XBridge C18 column
washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 30 mL/min)

Sources & evidence

ORD record: ord-81749cea5fe048519e9941f2dedd375f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290514B2

Reaction notes

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