Dimethylformamide → HCID 67253846, compound

HRID 1947983Notes

Reaction equation

HRID 1947983 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[NH2:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[CH2:7][C:6]=2[C:5]([C:14]#[N:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 534084597-Amino-4-bromo-2-methylisoindolin-1-one

Product 1

HCID 67253846HCID 67253846, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 7-Amino-4-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one (100.0 mg, 0.4148 mmol), zinc cyanide (48.71 mg, 0.4148 mmol) and Pd(PPh3)4 (71.90 mg, 0.06222 mmol) in DMF (1.5 mL, 19 mmol) was evacuated and purged with N2 three times. The mixture was heated in microwave at 150° C. for 5 minutes. The crude mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was evaporated and purified on an ISCO Combiflash unit to isolate the title compound (50.0 mg, 64% yield). MS (ES+): m/z 188.14 (100) [MH+]; HPLC: tR=1.00 min (UPLC, analytical).

Workup

  1. customwas evacuated
  2. custompurged with N2 three times
  3. additionThe crude mixture was diluted with ethyl acetate
  4. washwashed with water and brine
  5. customThe organic layer was evaporated
  6. custompurified on an ISCO Combiflash unit

Sources & evidence

ORD record
ord-6e5059f8ca3741439ff501e2b9d6010d
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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