Cesium carbonate → HCID 178495615, compound

HRID 1888224Notes

Reaction equation

HRID 1888224 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[OH:28][CH2:29]C1C=C(B(O)O)C=CC=1.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>[OH:28][CH2:29][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:15][CH2:16][N:17]([S:20]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])(=[O:21])=[O:22])[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 178495614HCID 178495614, compound2×

Product 1

HCID 178495615HCID 178495615, compoundYield 67.5%

Reagents, catalysts & solvents 2

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

Procedure

Following the general procedure of Example 65, a mixture of 5-bromo-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 25) (30 mg, 0.065 mmol), [3-(hydroxymethyl)phenyl]boronic acid (40 mg, 0.26 mmols), cesium carbonate (42.5 mg, 0.13 mmol), and Pd(PPh3)4 (22 mg) in dioxane/water (2 mL/0.7 mL) was reacted. The reaction mixture was concentrated, redissolved in methylene chloride and filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (18.0 mg, 14%)

Workup

  1. customwas reacted
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionredissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified
  7. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3f20baa62f5c4f5c8b4c3c1a385639a4
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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