Potassium Carbonate → HCID 178472574, compound

HRID 879441Notes

Reaction equation

HRID 879441 reaction equation
[F:1][C:2]1[C:10]2[C:5](=[CH:6][C:7](B3OC(C)(C)C(C)(C)O3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[C:20]([O:24][C@@H:25]([C:31]1[C:46]([CH3:47])=[CH:45][C:34]2[N:35]=[C:36]([C:38]3[CH:43]=[CH:42][N:41]=[C:40](Cl)[CH:39]=3)[S:37][C:33]=2[C:32]=1[C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:21].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:20]([O:24][C@@H:25]([C:31]1[C:46]([CH3:47])=[CH:45][C:34]2[N:35]=[C:36]([C:38]3[CH:43]=[CH:42][N:41]=[C:40]([C:7]4[CH:6]=[C:5]5[C:10]([C:2]([F:1])=[N:3][NH:4]5)=[CH:9][CH:8]=4)[CH:39]=3)[S:37][C:33]=2[C:32]=1[C:48]1[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetateHCID 178431019HCID 178431019, compound

Product 1

HCID 178472574HCID 178472574, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (prepared according to WO201059658, 48 mg, 0.184 mmol), (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (75 mg, 0.142 mmol) and 2M potassium carbonate solution (0.28 mL, 0.568 mmol) in dioxane (1.0 mL) was sparged with nitrogen for 10 minutes, Pd(PPh3)4 (16 mg, 0.014 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 C34H31ClFN4O3S: 629.2 (M+H+); Found: 629.3 (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-770c0cc167874238940c7f54fc383c41
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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