Triethylamine → HCID 69060737, compound

HRID 734852Notes

Reaction equation

HRID 734852 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[C:5]2[CH3:13].C(N(CC)CC)C.CN([CH:24]=[O:25])C.[CH3:26][OH:27]>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([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:26]([O:25][CH3:24])=[O:27])[CH:6]=[C:5]2[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 47381436-Bromo-2-chloro-4-methylquinolineHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 69060737HCID 69060737, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Procedure

A solution of 1.10 g (4.29 mmol) of 6-bromo-2-chloro-4-methylquinoline, 0.24 g (0.43 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 97 mg (0.43 mmol) of palladium (II) acetate, and 1.25 mL (9.00 mmol) of triethylamine in 60 mL of DMF/MeOH (1:1) was stirred for 10 minutes at 50° C. and under 2 bar CO pressure. The reaction mixture was evaporated down in vacuo, the residue was combined with EtOAc, the precipitate was filtered off, and the filtrate was evaporated down. The residue was purified by column chromatography (silica gel, gradient PE/EtOAc 8:2→6:4). Yield: 0.65 g (54% of theoretical); C12H10BrNO2 (M=280.117); calc: molpeak (M+H)+: 280/282 (Br); found: molpeak (M+H)+: 280/282 (Br); HPLC-MS: 8.55 minutes (method A).

Workup

  1. customThe reaction mixture was evaporated down in vacuo
  2. filtrationthe precipitate was filtered off
  3. customthe filtrate was evaporated down
  4. customThe residue was purified by column chromatography (silica gel, gradient PE/EtOAc 8:2→6:4)
  5. custom8.55 minutes (method A)

Sources & evidence

ORD record
ord-ed1a2da8575e400baf311b43f02667f7
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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