Ethyl Acetate → HCID 53492571, compound

HRID 705178Notes

Reaction equation

HRID 705178 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:29][C:26]([CH3:28])([CH3:27])[C:23]([CH3:25])([CH3:24])[O:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[CH3:27][C:26]1([CH3:28])[C:23]([CH3:24])([CH3:25])[O:22][B:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][O:12][C:10]3[CH:9]=[CH:8][C:6]4[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]=4[CH:11]=3)=[CH:20][CH:19]=2)[O:29]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 53492571HCID 53492571, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Cyano-6-hydroxybenzothiazole (300 mg, 1.7 mmol) and 4-(bromomethyl)benzeneboronic acid pinacol ester (505.7 mg, 1.7 mmol) were dissolved in 30 mL dry DMF prior to the addition of cesium carbonate (610.25 mg, 1.87 mmol). The mixture was stirred at 60° C. for 45-50 minutes before it was allowed to cool to room temperature. 100 mL EtOAc was added to the reaction mixture, and the organic phase was washed three times with deionized water (DI H2O). The aqueous layers were combined and washed three times with EtOAc. All of the organic layers were combined, washed twice with brine, dried over sodium sulfate, and concentrated. The crude material was purified on a silica column (90:10 hexanes:ethyl acetate, dry loaded) to give 547.4 mg (82%) of the pure product. 1H NMR (400 MHz, CDCl3): δ 1.36 (1H, s), 5.21 (2H, s), 7.32 (1H, d, J=8.8 Hz), 7.40 (1H, s), 7.45 (2H, d, J=7.6 Hz), 7.86 (2H, d, J=7.2 Hz), 8.09 (1H, d, J=9.2 Hz). LRESI-MS: calculated for [C21H22BN2O3S]+393.1. found 393.1.

Workup

  1. temperatureto cool to room temperature
  2. washthe organic phase was washed three times with deionized water (DI H2O)
  3. washwashed three times with EtOAc
  4. washwashed twice with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified on a silica column (90:10 hexanes:ethyl acetate, dry loaded)

Sources & evidence

ORD record
ord-a24394f919d04c5a8971680437a30ed7
Source dataset
uspto-grants-2015_11
Patent number
US09173966B2

Reaction notes

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