Sodium Carbonate → HCID 131732823, compound

HRID 572472Notes

Reaction equation

HRID 572472 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[C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17].[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[F:29].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:22])[C:28]=1[F:29])=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 131732824HCID 131732824, compound

Product 1

HCID 131732823HCID 131732823, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 4-Bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-isochromen-1-one (1.3 g, 3.53 mmol) in 15 ml of dioxane/H2O (5:1) was added 3,4-Difluorophenylboronic acid (0.83 g, 5.3 mmol) and Na2CO3(0.75 g, 7.06 mmol), then Pd(dppf)Cl2 (0.26 g, 0.35 mmol). Then the resultant mixture was stirred for 2 hours at 90° C. under N2. TLC showed SM was consumed, the reaction mixture was cooled to RT, removed the solvent, the residue was purified by column chromatography on silica gel eluted with (PE:EA=50:1) to afford title product. (m=1.3 g, yield=85%). 1HNMR: (400 MHz, CDCl3) δ 0.00 (s, 6 H), 0.83 (s, 9 H), 4.30 (tt, J=12 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 7.11 (t, J=6.0 Hz, 1H), 7.20 (m, 1H), 7.31 (tt, J=6.8 Hz, 1H), 7.54 (t, J=6.8 Hz, 1H), 7.64 (t, J=6.8 Hz, 1H), 8.36 (d, J=8.0 Hz, 1H).

Workup

  1. customwas consumed
  2. customremoved the solvent
  3. customthe residue was purified by column chromatography on silica gel
  4. washeluted with (PE:EA=50:1)

Sources & evidence

ORD record
ord-b5577b8223fa4fd898a5eacdb16e7177
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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