N-bromobutanimide → tert-butyl 5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate

HRID 1764909Notes

Reaction equation

[CH2:1]1[N:11]2[C:12]3[C:8]([CH:9]4[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[S:3][CH2:2]1.[Br:24]N1C(=O)CCC1=O>CN(C=O)C>[Br:24][C:6]1[CH:7]=[C:8]2[C:12]3=[C:4]([S:3][CH2:2][CH2:1][N:11]3[CH:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH:9]23)[CH:5]=1

Participants

Conditions

Temperature: -10 °C

Procedure

The tert-butyl 1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate (2.00 g, 6.02 mmol) was dissolved in anhydrous DMF (50 mL) and then cooled in an ice/acetone bath at −10° C. for 20 min. Next, N-bromosuccinimide (1.18 g, 6.62 mmol) was added in one portion. The reaction mixture was stirred for 40 min at −10° C., then poured over an ice/water mixture (300 mL). The resulting suspension was stirred at room temperature for 30 min, and extracted with diethyl ether (4×100 mL). The organic extracts were pooled together, washed with brine and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, tert-butyl 5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate was obtained as a yellow foam (2.24 g, 91%). 1H NMR (300 MHz, CDCl3) δ1.47 (s, 9H), 1.77 (m, 2H), 3.46-3.48 (m, 4H), 2.87-3.48 (m, 6H), 6.93 (s, 1H), 6.97 (s, 1H) ppm.

Workup

stirringThe resulting suspension was stirred at room temperature for 30 min
extractionextracted with diethyl ether (4×100 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
customAfter removing the solvent under reduced pressure

Sources & evidence

ORD record: ord-6042940bd5c0478dadee0d0a59d0a734
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039679E1

Reaction notes

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