Acetonitrile → HCID 57754727, compound

HRID 226958Notes

Reaction equation

HRID 226958 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH3:28])[CH:22]=3)=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.C([Sn](C(C)(C)C)(C(C)(C)C)[C:35]1[O:36][CH:37]=[CH:38][N:39]=1)(C)(C)C.C(#N)C>O1CCCC1.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>[CH3:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[CH3:27])[C:20]([C:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:35]3[O:36][CH:37]=[CH:38][N:39]=3)[N:7]=2)[CH:10]=1)=[O:29]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 16731006HCID 16731006, compoundHCID 68616802HCID 68616802, compound

Product 1

HCID 57754727HCID 57754727, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

90 mg (0.2 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 143 mg (0.40 mmol) of 2-tri-t-butylstannyloxazole, 23 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 2 mL of anhydrous tetrahydrofuran. The resultant mixture was stirred at 75° C. for 18 h. The reaction solution was quenched by pouring into a container having 20 mL of water. The crude product precipitated out of solution and was isolated by filtration. The crude product was purified by flash chromatography to yield 16 mg of 4nn as a colorless solid: LC-MSD, m/z for C27H21N3O3, [M+H]+=436.5, [M+2H]+=437.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.136 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.35 (d, 6H), 5.62 (s, 2H), 7.06 (d, 1H), 7.19 (d, 1H), 7.35-7.44 (m, 3H), 7.54-7.62 (m, 2H), 7.66 (s, 1H), 7.78 (t, 1H), 7.84 (d, 1H), 8.08 (d, 1H), 8.34 (s, 1H), 8.48 (d, 1H).

Workup

  1. customThe reaction solution was quenched
  2. additionby pouring into a container
  3. customThe crude product precipitated out of solution
  4. customwas isolated by filtration
  5. customThe crude product was purified by flash chromatography
  6. customto yield 16 mg of 4nn as a colorless solid

Sources & evidence

ORD record
ord-c956c382ac2746729fdace2c6c7a8faf
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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