Potassium Carbonate → HCID 18442489, compound

HRID 458937Notes

Reaction equation

HRID 458937 reaction equation
[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH3:22])[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[N+:23]([C:26]1[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C([O-])([O-])=O.[K+].[K+]>[Cu]I>[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH3:22])[C:11](=[O:12])[N:10]([C:29]2[CH:30]=[CH:31][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 18442491HCID 18442491, compound

Product 1

HCID 18442489HCID 18442489, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
200 °C

Procedure

To 3,3-dibutyl-4-oxo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (synthesised by the procedure of WO9616051 for the corresponding 3-butyl-3-ethyl analogue; 2.9 g, 9.0 mmol) was added p-nitrophenylbromide (24 g, 119 mmol), K2CO3 (1.6 g, 12 mmol) and CuI (180 mg, 0.95 mmol). The reaction mixture was heated to 200° C. overnight. Then it was allowed to cool down to room temperature and the resulting solid was purified by chromatography using DCM as eluent. The fractions containing the product were concentrated under reduced pressure and EtOH (95%) was added and the insoluble p-nitrophenylbromide was then filtered off. The residue was purified again by flash chromatography using DCM as eluent. The product was still not pure so the residue was then purified by flash chromatography using EtOAc:heptane, 1:9 as eluent to give the title compound 2.57 g (64%). NMR (600 MHz) 0.77–0.87 (m, 6H), 1.12–1.31 (m, 8H), 1.4–1.6 (m, 4H), 3.09 (brs, 2H), 3.79 (s, 3H), 6.72–6.83 (m, 2H), 7.18–7.27 (m, 3H), 8.3 (d, 2H).

Workup

  1. temperatureto cool down to room temperature
  2. customthe resulting solid was purified by chromatography
  3. additionThe fractions containing the product
  4. concentrationwere concentrated under reduced pressure and EtOH (95%)
  5. additionwas added
  6. filtrationthe insoluble p-nitrophenylbromide was then filtered off
  7. customThe residue was purified again by flash chromatography
  8. customwas then purified by flash chromatography

Sources & evidence

ORD record
ord-c4d7217a6bfc4c70a442b5826fb680f3
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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