Sodium Carbonate → HCID 58464845, compound

HRID 2089423Notes

Reaction equation

HRID 2089423 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[N:18]1([C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[K+]>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].C(#N)C>[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:25]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 17982644[3-(Piperidin-1-yl)phenyl]boronic acidHCID 58464823HCID 58464823, compound

Product 1

HCID 58464845HCID 58464845, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a microwave reaction vial was added 317 from Example 317 (150 mg, 0.51 mmol), 3-(piperidin-1-yl)phenylboronic acid (312 mg, 1.52 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (41 mg, 0.051 mmol), a 1M solution of Na2CO3 (0.76 mL), a 1M solution of potassium acetate (0.76 mL) and acetonitrile (11 mL). The mixture was irradiated to 120° C. with a microwave for 30 min and cooled to room temperature. It was filtered through Celite and thoroughly washed with methylene chloride. The filtrate was concentrated and the residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide). The product was further purified via reverse phase HPLC to afford 318. 1H NMR (400 MHz, DMSO) δ 10.34 (s, 1H), 8.07 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.71 (s, 1H), 7.59-7.43 (m, 2H), 7.34-7.17 (m, 2H), 7.03-6.84 (m, 3H), 3.83 (s, 3H), 3.26-3.18 (m, 4H), 1.73-1.48 (m, 7H). MS (ESI) m/z: 377.2 [M+H+].

Workup

  1. customTo a microwave reaction
  2. customThe mixture was irradiated to 120° C. with a microwave for 30 min
  3. filtrationIt was filtered through Celite
  4. washthoroughly washed with methylene chloride
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide)
  7. customThe product was further purified via reverse phase HPLC

Sources & evidence

ORD record
ord-c0b2708c4fc34ba4a5a84ad6b5a3cdbc
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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