Dimethylformamide → HCID 70817573, compound

HRID 82085Notes

Reaction equation

HRID 82085 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[N:6][CH:7]=1.[CH3:32][N:33](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:32]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[N:6][CH:7]=1)#[N:33]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 708176032-(5-bromopyridin-2-yl)-N-(5-{[7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)acetamide

Product 1

HCID 70817573HCID 70817573, compoundYield 18%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Zinc cyanide (28 mg, 0.23 mmol) was added to 2-(5-Bromo-pyridin-2-yl)-N-[5-(7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-acetamide (Example 317, 75 mg, 0.16 mmol) in DMF (2 mL) and the mixture was degassed with argon for 10 minutes. Then tris(dibenzylideneacetone)dipalladium (3 mg, 0.003 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (7 mg, 0.012 mmol) were added and the mixture was heated at 100° C. for 40 mins under microwave irradiation. The mixture was diluted with EtOAc (5 mL) and washed with water (2 mL), brine (2 mL) and dried over sodium sulphate. The filtrate was evaporated in vacuo and purified by preparative TLC (3% MeOH in DCM) to afford the title compound as a light brown solid in 18% yield, 12 mg.

Workup

  1. customthe mixture was degassed with argon for 10 minutes
  2. washwashed with water (2 mL), brine (2 mL)
  3. dry with materialdried over sodium sulphate
  4. customThe filtrate was evaporated in vacuo
  5. custompurified by preparative TLC (3% MeOH in DCM)

Sources & evidence

ORD record
ord-e0124d4618914b0a97bd8c95fb007273
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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