Potassium bisulfate → HCID 57500360, compound

HRID 2273535Notes

Reaction equation

HRID 2273535 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:11][C:12]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[N:32]3[C:27]([CH:28]=[CH:29][CH:30]=[CH:31]3)=[C:26]([OH:33])[C:25]=2[CH3:34])=[O:23])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].[C:35]([O:39][C:40](=[O:51])[CH2:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49]Br)[CH:44]=1)([CH3:38])([CH3:37])[CH3:36].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[NH2:11][C:12]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[N:32]3[C:27]([CH:28]=[CH:29][CH:30]=[CH:31]3)=[C:26]([O:33][CH2:49][C:45]3[CH:46]=[CH:47][CH:48]=[C:43]([O:42][CH2:41][C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:51])[CH:44]=3)[C:25]=2[CH3:34])=[O:23])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 516920Potassium bisulfateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22645499HCID 22645499, compoundHCID 57500359HCID 57500359, compound

Product 1

HCID 57500360HCID 57500360, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

5.43 ml (2.71 mmol) of potassium bis(trimethylsilyl)amide at −20° C. are added to the solution of 0.80 g (2.47 mmol) of methyl 2-amino-5-[(1-hydroxy-2-methylindolizin-3-yl)carbonyl]benzoate in 12 ml of tetrahydrofuran. After 15 minutes, 1.49 g (4.93 mmol) of tert-butyl[3-(bromomethyl)phenoxy]acetate (CAS 176673-59-9 described in Patent Application WO2004014366) in solution in 2 ml of tetrahydrofuran are added and the mixture is then heated at 40° C. for 12 hours. The reaction medium is poured into a saturated aqueous solution of potassium hydrogen sulphate, and the mixture is extracted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. After purification by flash chromatography on silica gel (toluene/ethyl acetate gradient=100/00 to 60/40), 0.92 g (61%) of a yellow oil is obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash chromatography on silica gel (toluene/ethyl acetate gradient=100/00 to 60/40)

Sources & evidence

ORD record
ord-3af1b94081d043f9942b94e68190ee0b
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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