Dimethylformamide → HCID 45139208, compound

HRID 1949118Notes

Reaction equation

HRID 1949118 reaction equation
Br[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=3)[NH:7][C:6]=2[C:5]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:4]2[NH:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=3[C:3]=12.[CH3:30][N:31](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>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][O:16][C:5]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][C:11]([F:15])=[CH:10][CH:9]=3)[C:14]=2[C:2]([C:30]#[N:31])=[C:3]2[C:28]3[CH:27]=[C:26]([F:29])[CH:25]=[CH:24][C:23]=3[NH:22][C:4]=12

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 59238889HCID 59238889, compound

Product 1

HCID 45139208HCID 45139208, compoundYield 46%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(12-bromo-2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (97.8 mg, 0.1991 mmol), zinc cyanide (233.7 mg, 1.9910 mmol) and tetrakis(triphenylphosphine)palladium (0) (23.0 mg, 0.01991 mmol) in anhydrous DMF was purged with high-purity Ar for five minutes, sealed with Teflon cap and heated to 160° C. for 12 hours. The reaction mixture was cooled down and filtered. The solvent was removed via vacuum pump. The residue was purified via flash chromatography to provide the title compound (37.3 mg, 46%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.90 (s, 2 H), 8.39 (dd, J=10.2, 2.8 Hz, 2 H), 7.55 (dd, 8.8, 4.4 Hz, 2 H), 7.31 (td, J=8.8, 2.4 Hz, 2 H), 4.33 (t, J=4.2 Hz, 2 H), 2.74 (t, J=4.2 Hz, 2 H), 2.35 (s, 6 H); MS (ESI) m/z 403.1 (M−H)−; MS (ESI) m/z 405.0 (M+H)+

Workup

  1. customwas purged with high-purity Ar for five minutes
  2. customsealed with Teflon
  3. customcap
  4. temperatureThe reaction mixture was cooled down
  5. filtrationfiltered
  6. customThe solvent was removed via vacuum pump
  7. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-264d08095b3a471f9053c070069cd06c
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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