Potassium Carbonate → HCID 86700262, compound

HRID 879453Notes

Reaction equation

HRID 879453 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C@@H:29]([C:35]1[C:50]([CH3:51])=[CH:49][C:38]2[N:39]=[C:40]([C:42]3[CH:47]=[CH:46][N:45]=[C:44](Cl)[CH:43]=3)[S:41][C:37]=2[C:36]=1[C:52]1[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][CH:53]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.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>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12]([C:44]2[CH:43]=[C:42]([C:40]3[S:41][C:37]4[C:36]([C:52]5[CH:53]=[CH:54][C:55]([Cl:58])=[CH:56][CH:57]=5)=[C:35]([C@H:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:50]([CH3:51])=[CH:49][C:38]=4[N:39]=3)[CH:47]=[CH:46][N:45]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 177502172-(Benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700262HCID 86700262, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (15 mg, 0.048 mmol), (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (17 mg, 032 mmol) and 2M potassium carbonate solution (48 μL, 0.096 mmol) in dioxane (0.5 mL) was sparged with nitrogen for 10 minutes, Pd(PPh3)4 (3.7 mg, 0.0032 mmol) was added and reaction mixture was heated at 100° C. for 4 h. Reaction mixture was diluted with ethyl acetate, washed with brine. The aqueous layer was back extracted with ethyl acetate and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 20% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C39H37ClN3O4S: 678.2 (M+H+); Found: 678.3 (M+H+).

Workup

  1. customwas sparged with nitrogen for 10 minutes
  2. customreaction mixture
  3. customReaction mixture
  4. washwashed with brine
  5. extractionThe aqueous layer was back extracted with ethyl acetate
  6. dry with materialthe combined organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by CombiFlash (0 to 20% EtOAc/Hex)
  10. customto give product

Sources & evidence

ORD record
ord-59f6be85bb924a11a7fa09211ac08c6e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…