Sodium Carbonate → HCID 86704620, compound

HRID 1508572Notes

Reaction equation

HRID 1508572 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28](I)[CH:27]=4)=[CH:24][N:23]=[C:22]([S:34][CH3:35])[N:21]=3)[C@H:14]2[CH3:36])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:39]([O-:42])([O-])=[O:40].[Na+].[Na+].O.[CH3:46]CO.[C:49]1([CH3:55])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>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>[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:50]5[CH:51]=[CH:52][C:53]([C:39]([O:42][CH3:46])=[O:40])=[CH:54][C:49]=5[CH3:55])[CH:27]=4)=[CH:24][N:23]=[C:22]([S:34][CH3:35])[N:21]=3)[C@H:14]2[CH3:36])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 86587398Ethanol toluene waterHCID 86704621HCID 86704621, compound

Product 1

HCID 86704620HCID 86704620, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of the title compound from Step B (400 mg, 0.596 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1-3,2-dioxaborolan-2-yl)benzoate (247 mg, 0.894 mmol), Na2CO3 (139 mg, 1.31 mmol) and catalytic amount of Pd(PPh3)4 was mixed in water/EtOH/toluene (1:2:4) (7 mL). The mixture was stirred at 80° C. for 1 h. The mixture was cooled, and the solvents were removed. Water (5 mL) was added and the mixture was extracted with dichloromethane (3×5 mL). The combined organic fractions were washed with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (2:8) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.47 (s, 1H), 8.02 (s, 1H), 7.96 (d, J=8 Hz, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.33 (m, 4H), 5.76 (d, J=8.0 Hz, 1H), 4.98 (d, J=17 Hz, 1H), 4.46 (m, 1H), 4.13 (d, J=17 Hz, 1H), 3.97 (s, 3H), 2.65 (s, 3H), 2.33 (s, 3H), 0.78 (d, J=6.5 Hz, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvents were removed
  3. additionWater (5 mL) was added
  4. extractionthe mixture was extracted with dichloromethane (3×5 mL)
  5. washThe combined organic fractions were washed with brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel Biotage 40S
  10. washeluting with EtOAc/hexane (2:8)

Sources & evidence

ORD record
ord-c95c447036ee4bc0adaa0c3a10d33b7a
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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