Water → HCID 86653304, compound

HRID 1695746Notes

Reaction equation

HRID 1695746 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19][C:20]1[N:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:12][C:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:20]([Cl:19])=[N:25][CH:24]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 58255771HCID 58255771, compoundHCID 86653303{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid

Product 1

HCID 86653304HCID 86653304, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

6-Bromo-1-methyl-1H-indazol-4-amine (340 mg), sodium carbonate (638 mg) and Pd(dppf)Cl2 (110 mg) were weighed to a 10-20 ml microwave vial. {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid (377 mg) dissolved in 1,4-dioxane (6 ml) was added followed by water (6 ml). The reaction was heated for 15 min at 120° C. in the microwave. The reaction was passed through a 2 g silica cartridge, washing with methanol. The solvent was evaporated under nitrogen blow down. The residue was purified on the ISCO companion using a 40 g silica cartridge and a gradient of 2-8% methanol in DCM (containing 1% ammonia) over 15 mins at 40 ml/min. Product-containing fractions were combined and dried down to give title compound (158 mg).

Workup

  1. additionwas added
  2. washwashing with methanol
  3. customThe solvent was evaporated under nitrogen blow down
  4. customThe residue was purified on the ISCO companion
  5. customdried down

Sources & evidence

ORD record
ord-96256255827443ccadac58741674420a
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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