N-bromobutanimide → HCID 136390253, compound

HRID 1046980Notes

Reaction equation

HRID 1046980 reaction equation
[N:1]1[C:2]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:3][N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.[Br:24]N1C(=O)CCC1=O>C1COCC1>[Br:24][C:3]1[N:4]2[C:5]3[CH:18]=[CH:17][CH:16]=[N:15][C:6]=3[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]2=[N:1][C:2]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 136390211HCID 136390211, compound

Product 1

HCID 136390253HCID 136390253, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)acetate (0.14 g, 1 eq.) in THF (10 mL) was added N-bromosuccinimide (0.077 g, 1 eq.). The reaction was stirred at room temperature for 30 minutes, poured onto water (30 mL) and extracted with ethyl acetate (2×30 mL). The organic extracts were combined, washed with water (1×50 mL), brine (1×50 mL) and dried over sodium sulfate. After filtration and concentration under reduced pressure, the crude product was purified by column chromatography (2-5% methanol in dichloromethane). The methyl 2-(3-bromo-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)acetate (0.162 g, 98%) was obtained. 1H NMR (DMSO-d6) 400 MHz δ 8.23 (dd, JA=4.4 Hz, JB=1.6 Hz, 1H), 7.96 (dd, JA=7.6 Hz, JB=1.6 Hz, 1H), 7.77 (dd, JA=8.0 Hz, JB=1.6 Hz, 1H), 7.38-7.33 (m, 1H), 7.19 (dd, JA=8.0 Hz, JB=4.8 Hz, 1H), 7.14-7.05 (m, 2H), 3.75 (s, 2H), 3.74 (s, 3H); LCMS: 385, 387 [M+H].

Workup

  1. additionpoured onto water (30 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washwashed with water (1×50 mL), brine (1×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. customthe crude product was purified by column chromatography (2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5955f8022bc04ca0ace9d9cce7e73339
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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