Water → HCID 18408150, compound

HRID 475277Notes

Reaction equation

HRID 475277 reaction equation
Br[C:2]1[C:10]([Cl:11])=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.O.[CH3:13][N:14]1C(=O)CCC1>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.[C-]#N.[C-]#N.[Zn+2]>[Cl:11][C:10]1[C:2]([C:13]#[N:14])=[CH:3][C:4]2[N:8]=[CH:7][NH:6][C:5]=2[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 203691691360953-55-4

Product 1

HCID 18408150HCID 18408150, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

A mixture of 248 (550 mg, 2.38 mmol), Pd(PPh3)4 (275 mg, 0.238 mmol), and Zn(CN)2 (279 mg, 2.38 mmol) in NMP (10 mL) was stirred under nitrogen atmosphere at 120° C. for 18 h. The reaction mixture was poured into water (50 mL), extracted with EtOAc (3×20 mL), and concentrated to dryness in vacuo. The crude was purified by SiO2 chromatography eluting with DCM:MeOH (12:1) to afford 217 mg (51.5%) of 6-chloro-1H-benzo[d]imidazole-5-carbonitrile (250) as yellow solid (217 mg, 51.5%): MS (ESI) m/z=178.2 (M+1).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. concentrationconcentrated to dryness in vacuo
  3. customThe crude was purified by SiO2 chromatography
  4. washeluting with DCM:MeOH (12:1)

Sources & evidence

ORD record
ord-233da9b2db8a4a308d330ce5e74e5465
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…