5-Formylfuran-2-boronic acid → HCID 59511785, compound

HRID 1157469Notes

Reaction equation

HRID 1157469 reaction equation
[CH:1]([C:3]1[O:4][C:5](B(O)O)=[CH:6][CH:7]=1)=[O:2].I[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[N:16]([CH2:30][C:31]([NH:33][CH:34]([CH3:36])[CH3:35])=[O:32])[C:15]2=[O:37]>O1CCCC1.S1C=CC=C1C([O-])=O.[Cu+].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>[CH:1]([C:3]1[O:4][C:5]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)[N:16]([CH2:30][C:31]([NH:33][CH:34]([CH3:35])[CH3:36])=[O:32])[C:15]3=[O:37])=[CH:6][CH:7]=1)=[O:2]

Participants

6

Reactant 2

HCID 27343555-Formylfuran-2-boronic acidHCID 68522555HCID 68522555, compound

Product 1

HCID 59511785HCID 59511785, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-formylfuran-5-boronic acid (118 mg, 0.84 mmol) (Frontier Scientific), copper (I) thiophene-2-carboxylate (136 mg, 0.72 mmol) (Frontier Scientific), and tetrakis(triphenylphosphine)palladium (75 mg, 10 mol %) were added to a solution of 2-[6-iodo-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.24) in tetrahydrofuran (10 mL) under Argon. The solution was stirred at room temperature for 2 h. The resulting mixture was concentrated in vacuo. The resulting oil was purified by chromatography on a silica gel with methanol:dichloromethane (1:19, v/v) as eluent to give 2-[6-(5-formylfuran-2-yl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (90 mg, 0.20 mmol, 31%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customThe resulting oil was purified by chromatography on a silica gel with methanol:dichloromethane (1:19, v/v) as eluent

Sources & evidence

ORD record
ord-10c22e7869514084bc6eea463f1e7bd6
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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