N-bromobutanimide → tert-butyl 5-bromo-6-cyclohexyl-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008963Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[S:19][C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:17][C:9]=3[N:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:27]N1C(=O)CCC1=O>C(Cl)Cl>[Br:27][C:11]1[N:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:9]2[CH:17]=[C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[S:19][C:8]=2[C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 6-cyclohexyl-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1 eq., from Step 2) was dissolved in anhydrous CH2Cl2, cooled to 0° C. and treated portionwise over 40 mins with N-bromosuccinimide (1 eq.). The reaction mixture was quenched by the addition of 1 M sodium thiosulfate solution and extracted with EtOAc. The combined organic layers were washed with 1 M sodium thiosulfate solution and with brine and dried over sodium sulfate. Evaporation afforded the pure title compound (87%) as light-yellow foam. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 7.86 (s, 1H), 5.12 (s, 2H), 3.69 (s, 3H), 2.67-2.56 (m, 1H), 1.81-1.70 (m, 5H), 1.52 (s, 9H), 1.52-1.27 (m, 5H). MS (ES+) m/z: 456, 458 [M+H]+.

Workup

customThe reaction mixture was quenched by the addition of 1 M sodium thiosulfate solution
extractionextracted with EtOAc
washThe combined organic layers were washed with 1 M sodium thiosulfate solution and with brine
dry with materialdried over sodium sulfate
customEvaporation

Sources & evidence

ORD record: ord-cf52665d4990422dbd5200cc02e8ca60
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973026B2

Reaction notes

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