Potassium phosphate, tribasic, monohydrate → HCID 118131272, compound

HRID 634366Notes

Reaction equation

HRID 634366 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]3[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]3)[CH:25]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:28]1[CH:29]=[CH:24][CH:25]=[C:26]([CH:30]3[O:31][C:32]([CH3:38])([CH3:37])[C:33]([CH3:36])([CH3:35])[O:34]3)[CH:27]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

5

Reactant 3

HCID 22031701Potassium phosphate, tribasic, monohydrateHCID 78265135HCID 78265135, compoundHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 118131272HCID 118131272, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 4.05 g, 15.05 mmol), 4,4,5,5-tetramethyl-2-(3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-1,3,2-dioxaborolane (Intermediate G2, 5 g, 15.05 mmol), X-Phos-Pd-G2 (1.184 g, 1.505 mmol) and K3PO4.H2O (9.81 g, 30.1 mmol) were dispersed in THF (42 ml) and deoxygenated under argon, then water (42 mL) was added and the mixture stirred at rt overnight. The reaction was diluted with AcOEt (250 ml) and washed with 0.2 M of HClaqueous (250 ml), once with saturated NaClaqueous, anhydrified over Na2SO4 and the solvent removed under reduced pressure. The crude was purified via flash chromatography on silica gel using a Biotage 100G+50 G SNAP with a gradient of hexane and AcOEt to give the title compound (5.4 g, 91%) as dark oil.

Workup

  1. customdeoxygenated under argon
  2. additionwater (42 mL) was added
  3. additionThe reaction was diluted with AcOEt (250 ml)
  4. washwashed with 0.2 M of HClaqueous (250 ml)
  5. customonce with saturated NaClaqueous, anhydrified over Na2SO4 and the solvent removed under reduced pressure
  6. customThe crude was purified via flash chromatography on silica gel using a Biotage 100G+50 G SNAP with a gradient of hexane and AcOEt

Sources & evidence

ORD record
ord-202a1e8033114cdca522aabc29183f9d
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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