Potassium Carbonate → HCID 59410232, compound

HRID 2382690Notes

Reaction equation

HRID 2382690 reaction equation
[Cl:1][C:2]1[C:3](C2OC(C)(C)C(C)(C)O2)=[CH:4][C:5]([S:9]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[CH:20][CH:21]=[CH:22][C:13]2=3)(=[O:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.Br[C:33]1[C:34]([CH3:41])=[CH:35][C:36]([C:39]#[N:40])=[N:37][CH:38]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([S:9]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[CH:20][CH:21]=[CH:22][C:13]2=3)(=[O:11])=[O:10])=[CH:4][C:3]=1[C:33]1[C:34]([CH3:41])=[CH:35][C:36]([C:39]#[N:40])=[N:37][CH:38]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 533954685-Bromo-4-methylpyridine-2-carbonitrileHCID 68468098HCID 68468098, compound

Product 1

HCID 59410232HCID 59410232, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-4-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-yl)-phenol (153.0 mg, 0.33 mmol), 5-bromo-4-methyl-pyridine-2-carbonitrile (60 mg, 0.30 mmol), Pd(Ph3P)4 (38 mg, 0.03 mmol) and K2CO3 (138 mg, 1.0 mmol) in a mixture of dioxane (4 mL) and water (0.4 mL) was degassed with N2 for 5 min. The reaction vessel was sealed and then heated at 100° C. for 16 hrs. The mixture was then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was washed with brine (2×10 mL) and dried over MgSO4. After filtration and concentration, the material was purified by TLC plates eluting with ethyl acetate in hexanes (1/3) to give 5-[2-chloro-4-hydroxy-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-4-methyl-pyridine-2-carbonitrile 8-1 as a white solid (100 mg). MS: 453.9 (M+H)+; tR=8.37 min (method 2).

Workup

  1. customwas degassed with N2 for 5 min
  2. customThe reaction vessel was sealed
  3. customThe mixture was then partitioned between ethyl acetate (20 mL) and water (10 mL)
  4. washThe organic layer was washed with brine (2×10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration
  7. customthe material was purified by TLC plates
  8. washeluting with ethyl acetate in hexanes (1/3)

Sources & evidence

ORD record
ord-ed222b35cf514c36af25e0b8b14a0b56
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

Loading…