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Dimethylformamide → HCID 58746070, compound

HRID 2110489
Notes
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Reaction equation

HRID 2110489 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]2[N:10]([N:15]=[CH:16][CH:17]=2)[C:11](I)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]2[N:10]([N:15]=[CH:16][CH:17]=2)[C:11]([C:19]#[N:20])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58746000HCID 58746000, compound

Product 1

HCID 58746070HCID 58746070, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of (7-iodo-pyrazolo[1,5-a]pyridin-4-yl)-carbarnic acid tert-butyl ester (36 mg, 0.1 mmol), zinc cyanide (24 mg, 0.2 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), and anhydrous DMF (1 mL) was degassed with argon. Then, the mixture was stirred at 80° C. for 4.5 h, cooled to rt, mixed with EtOAc (6 mL), and filtered. The filtrate was concentrated under reduced pressure. Purification by silica gel flash chomatography eluting with EtOAc/heptane (gradient from 1:4 to 1:2 ratio) gave compound 777E (24 mg, 93%) as a white solid. HPLC: 93% at 3.64 min (retention time) (YMC S5 ODS-A column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): mn/z 259 [M+H]+.

Workup

  1. customwas degassed with argon
  2. temperaturecooled to rt
  3. additionmixed with EtOAc (6 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customPurification by silica gel flash chomatography
  7. washeluting with EtOAc/heptane (gradient from 1:4 to 1:2 ratio)

Sources & evidence

ORD record
ord-51a19d17e9634b61b82497e20caeeaaf
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07517904B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes