Potassium Carbonate → HCID 86700375, compound

HRID 879552Notes

Reaction equation

HRID 879552 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7](B(O)O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Br[C:15]1[N:16]=[C:17]([C:20]2[S:21][C:22]3[C:28]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)=[C:27]([C@H:36]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]([CH3:47])=[CH:25][C:23]=3[N:24]=2)[S:18][CH:19]=1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=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.O>[C:43]([O:42][C@@H:36]([C:27]1[C:26]([CH3:47])=[CH:25][C:23]2[N:24]=[C:20]([C:17]3[S:18][CH:19]=[C:15]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:2]([CH3:1])[N:3]=[CH:4]5)[N:16]=3)[S:21][C:22]=2[C:28]=1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:37]([O:39][CH2:40][CH3:41])=[O:38])([CH3:44])([CH3:45])[CH3:46]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 86700281HCID 86700281, compound

Product 1

HCID 86700375HCID 86700375, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

In a 10 mL reaction vial, 1-methyl-1H-indazol-5-ylboronic acid (31 mg, 0.173 mmol) and (S)-ethyl 2-(2-(4-bromothiazol-2-yl)-7-(4chlorophenyl)-5methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (100 mg, 0.173 mmol) were mixed with dioxane (5 mL) and water (1 mL). The resulting reaction mixture was bubbled with argon for 5 min. Then potassium carbonate (60 mg, 0.432 mmol) and Pd(PPh3)4 were added sequentially. The reaction mixture was sealed and heated in oil bath at 95° C. for 2 h. The brown mixture was then diluted with EtOAc (20 mL), filtered and the filtrate was concentrated and purified on silica gel column with 0-30% EtOAc/Hex to afford the title compound. LCMS-ESI+: calc'd for: C33H31ClN4O3S2: 631.2, 633.2, 632.2 (M+H+); found: 631.0, 633.1, 632.1 (M+H+).

Workup

  1. customIn a 10 mL reaction vial
  2. customThe resulting reaction mixture
  3. customwas bubbled with argon for 5 min
  4. customThe reaction mixture was sealed
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. custompurified on silica gel column with 0-30% EtOAc/Hex

Sources & evidence

ORD record
ord-ee178618b66c4d758396df7e26f8e710
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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