Dimethylformamide → HCID 67076708, compound

HRID 2094723Notes

Reaction equation

HRID 2094723 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH:19]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11](Br)[CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].COC(C)(C)C.[CH3:43][N:44](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>[CH2:1]([O:3][C:4]([C:6]1([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH:19]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:43]#[N:44])[CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 15413tert-Butyl methyl etherHCID 67076689HCID 67076689, compound

Product 1

HCID 67076708HCID 67076708, compound

Reagents, catalysts & solvents 2

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

Procedure

The compound of step 1 (50 mg, 0.091 mmol) was added to a mixture of zinc cyanide (10.6 mg, 0.091 mmol) and tetrakis(triphenylphosphine)palladium(0) (5.2 mg, 0.004 mmol) in DMF (0.16 ml) at 150° C. and stirred for 2 h. After cooling, tert-butyl methyl ether was added and the mixture was filtered over celite. The filtrate was washed with water, the organic phase dried over magnesium sulfate, filtered and evaporated to dryness to yield the title compound which was used without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered over celite
  3. washThe filtrate was washed with water
  4. dry with materialthe organic phase dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d3f2554aff414b4cbb9b5a6cbc17149e
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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