Sodium Carbonate → HCID 86625350, compound

HRID 1986196Notes

Reaction equation

HRID 1986196 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.[Li].C(OB(OC(C)C)OC(C)C)(C)C.[Cl:39][C:40]1[N:45]=[C:44](Cl)[C:43]([CH3:47])=[CH:42][N:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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.O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([C:42]3[C:43]([CH3:47])=[CH:44][N:45]=[C:40]([Cl:39])[N:41]=3)[S:13][C:12]=2[CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 21531Triisopropyl borateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 45051747Lithium diisopropylamineHCID 68858524HCID 68858524, compound

Product 1

HCID 86625350HCID 86625350, compoundYield 20%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Benzo[b]thiophen-6-yl-carbamic acid tert-butyl ester (1.06 g, 4.30 mmol) is dissolved in THF (40 mL) and cooled to −78° C. Lithium diisopropylamine solution (8.5 mL of 2.0 M solution) and triisopropylborate (6.0 mL, 26 mmol) are added. The reaction is stirred at −78° C. for 90 minutes before the cooling bath is removed. After stirring for three hours, 2,4-dichloro-5-methylpyrimidine (0.74 g, 4.5 mmol), 1,1′-bis(diphenylphosphino) ferrocene (120 mg, 0.220 mmol), palladium (II) acetate (50.4 mg, 0.220 mmol), and sodium carbonate (9.5 mL of 2.0 N solution) are added. The reaction is heated at 70° C. for 20 hours. After the reaction solution is cooled to 25° C., water (100 mL) is added. The mixture is extracted with dichloromethane and the extracts are evaporated. The resulting solid is chromatographed on silica gel, eluting with EtOAc in hexanes 5-50%, to give the title compound as a yellow solid (0.32 g, 20% yield).

Workup

  1. customis removed
  2. stirringAfter stirring for three hours
  3. temperatureThe reaction is heated at 70° C. for 20 hours
  4. temperatureAfter the reaction solution is cooled to 25° C.
  5. extractionThe mixture is extracted with dichloromethane
  6. customthe extracts are evaporated
  7. customThe resulting solid is chromatographed on silica gel
  8. washeluting with EtOAc in hexanes 5-50%

Sources & evidence

ORD record
ord-a317a8212a87443ca10505093afe76bb
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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