Cesium carbonate → HCID 11148787, compound

HRID 923638Notes

Reaction equation

HRID 923638 reaction equation
[S:1]1(=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2N=C1.CC[N:13]([CH:17](C)C)C(C)C.C([O-])([O-])=[O:21].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[O:21]=[C:17]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][N:13]1[CH2:27][C:28]([O:30][CH3:31])=[O:29]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 53400715Benzothiazolinone

Product 1

HCID 11148787HCID 11148787, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzothiazolone 1 (500 mg, 3.31 mmol) was suspended in CH2Cl2 (25 mL) containing DIEA (1.28 kg, 9.93 mmol) and Cs2CO3 (1.75 kg, 3.30 mmol). Methyl 2-bromoacetate (800 mg, 5.26 mmol) was then added at room temperature. The mixture was stirred for 5 h, concentrated under reduced pressure, and purified by chromatography on a silica gel column with elution of EtOAc/hexane (1:2) to give the title compound (495 mg, 67% yield). C10H9NO3S; white solid; mp 89-91° C.; 1H NMR (400 MHz, CDCl3) δ 8.15 (1H, dt, J=8, 0.8 Hz), 7.59 (1H, td, J=7.2, 1.2 Hz) 7.52 (1H, dt, J=8, 0.8 Hz) 7.37 (1H, td, J=7.2, 1.2 Hz), 4.59 (2H, s), 3.76 (3H, s); 13C NMR (100 MHz, CDCl3) δ 167.8, 165.4, 140.6, 132.0, 126.7, 125.4, 123.2, 120.2, 52.6, 44.5; ESI-HRMS calcd for C10H9NO3S: 224.0381. found: m/z 224.0390 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by chromatography on a silica gel column with elution of EtOAc/hexane (1:2)

Sources & evidence

ORD record
ord-9085f860bb274e3ab3890c69ae866039
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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