Dichloromethane → HCID 53237067, compound

HRID 1897600Notes

Reaction equation

HRID 1897600 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:20]1[C:21]2[CH:28]([CH3:29])[O:27][C:26](=[O:30])[C:22]=2[CH:23]=[N:24][CH:25]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[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]>[Cl:1][C:2]1[CH:9]=[C:8]([C:20]2[C:21]3[CH:28]([CH3:29])[O:27][C:26](=[O:30])[C:22]=3[CH:23]=[N:24][CH:25]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 579261132-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 69937523HCID 69937523, compound

Product 1

HCID 53237067HCID 53237067, compoundYield 15.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (116 mg, 0.44 mmol), 7-bromo-1-methylfuro[3,4-c]pyridin-3(1H)-one (100 mg, 0.44 mmol) and PdCl2(dppf).CH2Cl2 (28.6 mg, 0.035 mmol) in DMF (5 mL) was added a solution of Na2CO3 (0.44 mL, 2M) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. The mixture was warmed up room temperature, and solvent was removed in vacuo. The residue was dissolved in DCM and saturated NH4Cl solution. After extraction with DCM and separation, the combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by ISCO 40 g (10% MeOH/DCM, v/v, 0-25%) to give 19 mg of the titled compound. ESI-MS m/z: 284.9 [M+1]+, Retention time 1.32 min; 1H-NMR (MeOD, 400 MHz) δ 1.31 (d, J=6.8 Hz, 3H), 6.23 (q, J=6.8 Hz, 1H), 7.79 (dd, J=8.0, 1.6 Hz, 1H), 8.01 (d, J=1.6 Hz, 1H), 8.04 (d, J=8.0 Hz, 1H), 8.94 (s, 1H), 9.17 (s, 1H).

Workup

  1. temperatureThe mixture was warmed up room temperature
  2. customsolvent was removed in vacuo
  3. dissolutionThe residue was dissolved in DCM
  4. extractionAfter extraction
  5. customwith DCM and separation
  6. dry with materialthe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by ISCO 40 g (10% MeOH/DCM, v/v, 0-25%)

Sources & evidence

ORD record
ord-58181153f8ad4fffbef5c631d6537ec2
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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