Cesium carbonate → HCID 178451816, compound

HRID 1888289Notes

Reaction equation

HRID 1888289 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6](Br)[CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:3].[CH3:27][S:28]([NH:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:30])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+]>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>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([NH:31][S:28]([CH3:27])(=[O:29])=[O:30])[CH:37]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27735353-Methylsulfonylaminophenylboronic acidHCID 178451813HCID 178451813, compound2×

Product 1

HCID 178451816HCID 178451816, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indazol-3-yl]-1-piperidinecarboxylate (Intermediate 5) (30 mg, 0.07 mmols), {3-[(methylsulfonyl)amino]phenyl}boronic acid (46 mg, 0.21 mmols), cesium carbonate (150 mg), and Pd(PPh3)4 (10 mg) in dioxane/water (3/1, 4 mL) was heated at 160° C. for 2700 secs. (microwave irradiation). The resulting mixture was concentrated, redissolved in methylene chloride and filtered. The filtrate was concentrated and used in the next step without further purification.

Workup

  1. custom(microwave irradiation)
  2. concentrationThe resulting mixture was concentrated
  3. dissolutionredissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-0e9100d36a1e4f78b556c2a0b7d3d2d2
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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