Potassium Carbonate → HCID 70208312, compound

HRID 442781Notes

Reaction equation

HRID 442781 reaction equation
[NH2:1][C:2]1[C:6]2=[N:7][C:8](Cl)=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].C(B(CC)[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[NH2:1][C:2]1[C:6]2=[N:7][C:8]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 107527153-Amino-5-chlorothieno[3,2-b]pyridine-2-carboxylic acid methyl ester

Product 1

HCID 70208312HCID 70208312, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of the methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate prepared as described in Example 5A (0.252 g), diethyl 3-pyridyl-borane (0.155 g), Pd(dppf)Cl2 (0.082 g) and K2CO3 (420 mg) in degassed DMF (5 mL) was heated to 95° C. for 1.5 h, cooled, quenched in sat'd NH4Cl, the solid precipitate collected and chromatographed 9:1 hexane/EtOAc to give 0.24 g (81%) of the title compound: 1H NMR (300MHz, CDCl3) δ 3.95 (3H, s), 6.30 (2H, br s), 7.45 (1H, dd), 7.86 (1H, d), 8.19 (1H, d), 9:1 hexane/EtOAc to give 0.24 g (81%) of the title compound: 1H NMR (300MHz, CDCl3) δ 3.95 (1H, dd), 9.32 (1H, br d).

Workup

  1. temperaturecooled
  2. customquenched in sat'd NH4Cl
  3. customthe solid precipitate collected
  4. customchromatographed 9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-3a371e29ed134ff6b2a62ebb6403236d
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

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