Water → HCID 67520875, compound

HRID 1925759Notes

Reaction equation

HRID 1925759 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25])[CH2:16][O:17][CH3:18])(=[O:14])=[O:13].[C:28](=[O:31])([O-])[O-].[Cs+].[Cs+].[C:34]1(C)[CH:39]=CC=C[CH:35]=1.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([S:12]([N:15]([C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([O:26][CH3:27])=[O:25])[CH2:16][O:17][CH3:18])(=[O:14])=[O:13])=[C:2]([CH:35]=[CH:34][CH2:39][O:31][CH3:28])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 10796Cesium carbonateHCID 59180400HCID 59180400, compound

Product 1

HCID 67520875HCID 67520875, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Synthesized as described for 7 using 6 (300.0 mg, 0.65 mmol), cesium carbonate (634.0 mg; 1.95 mmol), (E)-2-(3-methoxyprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane (193.0 mg; 0.97 mmol), tetrakis(triphenylphosphine)palladium(0) (37.0 mg; 0.032 mmol), toluene (1.5 mL), water (1.5 mL) and ethanol (1.5 mL). The crude dark oil was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 20% v/v gradient elution over 500 mL) to give the title compound as a yellow oil (189 mg).

Workup

  1. customSynthesized
  2. customThe crude dark oil was purified by automated silica gel column chromatography (Biotage®)
  3. washeluting with ethyl acetate/hexanes (0 to 20% v/v gradient elution over 500 mL)

Sources & evidence

ORD record
ord-d56fcce71c3c4578a71ba519b46dd675
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

Loading…