Sodium Carbonate → HCID 59557789, compound

HRID 1174549Notes

Reaction equation

HRID 1174549 reaction equation
Br[C:2]1[S:3][C:4]2[C:5](=[O:14])[NH:6][CH2:7][C:8]([CH3:13])([CH3:12])[CH2:9][C:10]=2[N:11]=1.CC1(C)C(C)(C)OB([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:12][C:8]1([CH3:13])[CH2:7][NH:6][C:5](=[O:14])[C:4]2[S:3][C:2]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:11][C:10]=2[CH2:9]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59557796HCID 59557796, compound

Product 1

HCID 59557789HCID 59557789, compound

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-bromo-5,6,7,8-tetrahydro-7,7-dimethylthiazolo[5,4-c]azepin-4-one (200 mg, 1.0 Eq.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (224 mg, 1.5 Eq.), Pd(DBA)2 (42 mg, 0.1 Eq.) and sodium carbonate (2M aq., 1090 μl, 3.0 Eq.) were suspended/dissolved in dioxane (4 mL). The system was degassed using vacuum/N2 cycles three times. P(tBu)3 (42 mg, 0.1 Eq.) was then added and the reaction mixture stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature. The reaction mixture was partitioned in EtOAc/H2O and filtered through celite, which was washed copiously with EtOAc/H2O. The filtrate was partitioned and the aqueous was extracted with EtOAc (3×20 mL). The combined organics were washed with sat. aq. Na2CO3 (1×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (5% MeOH/95% EtOAc, followed by recrystallization from EtOAc/Hexanes gave the title compound was isolated as a brown powder (19.6 mg, 10% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 3.0 (4H, m), 7.7-7.8 (2H, d), 8.3 (1H, br m), 8.7-8.8 (2H, d); LC/MS M+1 (obs.) 274.60; LC/MS M−1 (obs.) 272.80.

Workup

  1. customThe system was degassed
  2. temperatureto cool to room temperature
  3. customThe reaction mixture was partitioned in EtOAc/H2O
  4. filtrationfiltered through celite, which
  5. washwas washed copiously with EtOAc/H2O
  6. customThe filtrate was partitioned
  7. extractionthe aqueous was extracted with EtOAc (3×20 mL)
  8. washThe combined organics were washed with sat. aq. Na2CO3 (1×20 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customPurification by column chromatography (5% MeOH/95% EtOAc
  13. customfollowed by recrystallization from EtOAc/Hexanes

Sources & evidence

ORD record
ord-c0079e39ad96484ca3d68ad8cb861f93
Source dataset
uspto-grants-2010_11
Patent number
US07838517B2

Reaction notes

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