Sodium Acetate → HCID 11535765, compound

HRID 604369Notes

Reaction equation

HRID 604369 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])(=O)C.[Na+]>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]>[S:3]1[C:2]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:7](=[O:9])[C:6]=2[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2773216(2-Aminophenyl)boronic acidHCID 53302196Methyl 2-bromothiophene-3-carboxylate

Product 1

HCID 11535765HCID 11535765, compoundYield 12%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 64 mg, 0.29 mmol), 2-amino phenyl boronic acid (1.2 eq, 48 mg, 0.35 mmol), sodium acetate (3.0 eq, 71 mg, 0.86 mmol) and PdCl2(dppf) (0.1 eq, 15 mg, 0.028 mmol) were mixed together in anhydrous DMF (0.2 ml). The mixture was heated in a microwave oven at 120° C. for 5 nm. The material was purified by preparative HPLC. Acetonitrile was evaporated, and the compound was extracted with CH2Cl2 (3×). The combined extracts were washed with water, dried over Na2SO4, and the solvents removed in vacuo. Recrystallization in EtOH provided thieno[3,2-c]quinolin-4(5H)-one as a tan crystalline solid (7 mg, 12% yield). LCMS (ES): 95% pure, m/z 202 [M+1]+; 1H NMR (CDCl3/CD3OD, 9:1, 400 MHz) δ 7.28 (m, 1H), 7.33 (m, 1H), 7.43-7.50 (m, 2H), 7.74 (d, J=4.4, 1H), 7.82 (d, J=7.6, 1H) ppm

Workup

  1. customThe material was purified by preparative HPLC
  2. customAcetonitrile was evaporated
  3. extractionthe compound was extracted with CH2Cl2 (3×)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvents removed in vacuo
  7. customRecrystallization in EtOH

Sources & evidence

ORD record
ord-1bc109be9931464280e4f35a9dcd0aa9
Source dataset
uspto-grants-2011_03
Patent number
US07910600B2

Reaction notes

Loading…