Dimethylformamide → HCID 90409664, compound

HRID 589043Notes

Reaction equation

HRID 589043 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:21]2[C:22]([CH3:27])=[N:23][O:24][C:25]=2[CH3:26])[C:5]2[O:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:7]3[C:17](=[O:20])[NH:18][C:19]=1[C:6]=23.[CH3:28][N:29](C=O)C>CO.[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>[CH3:27][C:22]1[C:21]([C:4]2[C:5]3[O:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:7]4[C:17](=[O:20])[NH:18][C:19]([C:6]=34)=[C:2]([C:28]#[N:29])[CH:3]=2)=[C:25]([CH3:26])[O:24][N:23]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86299115HCID 86299115, compound

Product 1

HCID 90409664HCID 90409664, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

9-Bromo-7-(3,5-dimethylisoxazol-4-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (6.9 mg, 0.016 mmol), zinc cyanide (19 mg, 0.16 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.8 mg, 0.0024 mmol) were dissolved in DMF (1.6 mL) and the solution was deoxygenated. The stirred reaction mixture was heated at 150° C. in a microwave for 5 min. The mixture was diluted with MeOH and purified by preparative LCMS using pH 10 buffer to give the title compound. LCMS calc. for C21H17N4O3 (M+H)+: m/z=373.1. found: 373.2.

Workup

  1. customthe solution was deoxygenated
  2. customThe stirred reaction mixture
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-180bb2996c714fd7902950aa371bd41b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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