Sodium Carbonate → HCID 178483875, compound

HRID 2243592Notes

Reaction equation

HRID 2243592 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]2[O:8][C:9](I)=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[C:3]=1[OH:18].[CH3:19][N:20]([CH3:39])[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>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(Cl)Cl>[CH3:19][N:20]([CH3:39])[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:9]2[O:8][C:5]3[N:6]=[CH:7][C:2]([F:1])=[C:3]([OH:18])[C:4]=3[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 425989244-(2-(Dimethylamino)ethoxy)benzeneboronic acid, pinacol esterHCID 178516673HCID 178516673, compound

Product 1

HCID 178483875HCID 178483875, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

The mixture of 5-fluoro-2-iodo-3-phenyl-furo[2,3-b]pyridin-4-ol (5) (90.0 mg, 0.24, mmol), dimethyl-(2-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenoxy]-ethyl)-amine (114.0 mg, 0.39 mmol), LiCl (33.1 mg, 0.78 mmol), Pd(dppf)2Cl2 DCM (24.5 mg, 0.03 mmol) and Na2CO3 (0.33 mL, 2.0 M in water, 0.65 mmol) was degassed and heated to 80° C. with stirring under nitrogen for 5 h. The solvent was removed. The residue was purified by preparative HPLC to give the title compound. MS (m/z), M+H+ 393.2.

Workup

  1. customwas degassed
  2. customThe solvent was removed
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bdb9bd2142a242f9b4905239d432c905
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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