Dimethylformamide → HCID 18796965, compound

HRID 442779Notes

Reaction equation

HRID 442779 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:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.CN(C=O)C>CCOCC.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:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 107527153-Amino-5-chlorothieno[3,2-b]pyridine-2-carboxylic acid methyl ester

Product 1

HCID 18796965HCID 18796965, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate, prepared as described in Example 6A (0.243 g, 1.0 mmol), phenylboronic acid (0.134 g, 1.1 mmol) and triethylamine (0.20 mL) were added to 3 mL of DMF containing [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride (1:1 complex with CH2Cl2) under N2. The mixture was stirred at 90° C. for 4 h. The reaction was then cooled and diluted with Et2O. The organic layer was washed with H2O, brine, dried (MgSO4), concentrated and chromatographed (2:1 CH2Cl2 :hexane) to yield the title compound (140 mg, 50%): 1H NMR (300 MHz, CDCl3) δ 3.93 (s, 3H), 6.30 (bs, 2H), 7.41-7.55 (m, 3H), 7.84 (d, J=8 Hz, 1H), 8.07-8.13 (m, 3H); MS (DCI(NH3)) m/e 285 (M+H)+.

Workup

  1. temperatureThe reaction was then cooled
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (2:1 CH2Cl2 :hexane)

Sources & evidence

ORD record
ord-e504b282d1864c9d89223cbc00f89c72
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

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