Dimethylformamide → HCID 86345858, compound

HRID 1772698Notes

Reaction equation

HRID 1772698 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.[CH3:29][N:30](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>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([CH2:11][O:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:29]#[N:30])=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 117728336HCID 117728336, compound

Product 1

HCID 86345858HCID 86345858, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

A mixture of compound 31b (200 mg, 0.450 mmol), zinc cyanide (106 mg, 0.910 mmol), Pd(PPh3)4 (105 mg, 0.910 mmol) in DMF (5 mL) was heated to 80° C. for 4 h. The reaction was cooled to rt, filtered through a diatomaceous earth cartridge (2.5 g), and the filter cake was rinsed with EtOAc. The combined organic layers were concentrated under reduced pressure. The residue was recrystallized with hot EtOAc, collected by filtration, and dried to give compound 55a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C21H18N6O2: 387.2 [M+H]. found 387.2

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through a diatomaceous earth cartridge (2.5 g)
  3. washthe filter cake was rinsed with EtOAc
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customThe residue was recrystallized with hot EtOAc
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2587d1c3693846d692dfe10564fe2954
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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