Sodium Carbonate → HCID 59560104, compound

HRID 1643788Notes

Reaction equation

HRID 1643788 reaction equation
Br[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)=[O:16])[CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:10]=2)[CH:6]=1.[C:25](B(O)O)([CH3:27])=[CH2:26].C([O-])([O-])=O.[Na+].[Na+]>CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]([O:11][C:9]1[CH:10]=[C:4]2[O:3][C:2]([C:25]([CH3:27])=[CH2:26])=[CH:6][C:5]2=[C:7]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)=[O:16])[CH:8]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 59559933HCID 59559933, compound

Product 1

HCID 59560104HCID 59560104, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-bromo-6-isopropoxy-N-(5-methylpyridin-2-yl)benzofuran-4-carboxamide (263 mg, 0.68 mmol), isopropenyl boronic acid (58.4 mg, 0.68 mmol), Pd(PPh3)2Cl2 (23.9 mg, 0.034 mmol) and aqueous Na2CO3 (1.0 M in H2O, 1.36 mL) in 1.4 mL of CH3CN was heated in a microwave reactor at 150° C. for 5 min. The solvent was removed in vacuo. The residue was purified with Biotage column chromatography to give a light yellow solid (102 mg, 43% yield). 1H NMR (400 MHz, CDCl3) δ 9.07 (s, 1 H) 8.30 (d, J=8.56 Hz, 1 H) 7.96 (d, J=2.01 Hz, 1 H) 7.56 (dd, J=8.56, 2.27 Hz, 1 H) 7.26 (d, J=2.27 Hz, 1 H) 7.14 (d, J=1.51 Hz, 1 H) 7.09 (s, 1 H) 5.76 (s, 1 H) 5.17 (s, 1 H) 4.53-4.59 (m, 1 H) 2.27 (s, 3H) 2.11 (s, 3 H) 1.36 (d, J=6.04 Hz, 6 H); LCMS for C21H22N2O3 m/z 351.10 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified with Biotage column chromatography

Sources & evidence

ORD record
ord-83c75dd8a6fb43db9639c5f516f47739
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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