Potassium Carbonate → HCID 86700264, compound

HRID 879454Notes

Reaction equation

HRID 879454 reaction equation
[CH3:1][O:2][C:3]1[C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:18]([O:22][C@@H:23]([C:29]1[C:44]([CH3:45])=[CH:43][C:32]2[N:33]=[C:34]([C:36]3[CH:41]=[CH:40][N:39]=[C:38](Cl)[CH:37]=3)[S:35][C:31]=2[C:30]=1[C:46]1[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:21])([CH3:20])[CH3:19].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>[C:18]([O:22][C@@H:23]([C:29]1[C:44]([CH3:45])=[CH:43][C:32]2[N:33]=[C:34]([C:36]3[CH:41]=[CH:40][N:39]=[C:38]([C:8]4[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=4)[CH:37]=3)[S:35][C:31]=2[C:30]=1[C:46]1[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:19])([CH3:20])[CH3:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 177501662-Methoxy-3-(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 86700264HCID 86700264, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of 2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (13 mg, 0.0878 mmol), (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (31 mg, 0585 mmol) and 2M potassium carbonate solution (88 μL, 0.178 mmol) in dioxane (0.5 mL) was sparged with nitrogen for 10 minutes. Pd(PPh3)4 (6.9 mg, 0.0059 mmol) was added and reaction mixture was heated in microwave at 100° C. for 1 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 40% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C33H33ClN3O4S: 602.1 (M+H+); Found: 602.3 (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 40% EtOAc/Hex)
  10. customto give product

Sources & evidence

ORD record
ord-a38094eed5a84ea8bb4360fd2be288cf
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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