Sodium Carbonate → HCID 90411721, compound

HRID 1522029Notes

Reaction equation

HRID 1522029 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:10]([C:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH:13]=3)=[CH:11][C:3]=12.[F:32][C:33]1[CH:34]=[CH:35][C:36]([O:42][CH3:43])=[C:37](B(O)O)[CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[F:8][C:7]1[C:2]([C:35]2[CH:34]=[C:33]([F:32])[CH:38]=[CH:37][C:36]=2[O:42][CH3:43])=[C:3]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH:13]=3)[N:9]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:4]2=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90412725HCID 90412725, compound

Product 1

HCID 90411721HCID 90411721, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

To a solution of Example 279A (1250 mg, 2.86 mmol) in 13.3 mL tetrahydrofuran/water (3:1) was added 5-fluoro-2-methoxyphenylboronic acid (1043 mg, 3.72 mmol), sodium carbonate (1214 mg, 11.45 mmol) and phenylallylchloro[1,3-bix(diisopropylphenyl)-2-imidazol-2-ylidene]palladium(II) (60.3 mg, 0.086 mmol) and the mixture was heated at 75° C. for 2 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate, and the organics washed with saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (Analogix280, SF 40-80 column, 10-60% ethyl acetate/hexane gradient) gave the title compound. MS (ESI): 553.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washthe organics washed with saturated sodium bicarbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Analogix280, SF 40-80 column, 10-60% ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-43124c7b22184c0ebce0dcef4664c1ed
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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