Sodium Carbonate → HCID 46846845, compound

HRID 419768Notes

Reaction equation

HRID 419768 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:24])[NH2:23])[C:16]=3[N:17]=2)=[CH:9][CH:8]=1)(=O)=O.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O>[C:7]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:16](=[C:18]([C:22]([NH2:23])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:17]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 46846744HCID 46846744, compound

Product 1

HCID 46846845HCID 46846845, compound

Reagents, catalysts & solvents 1

HCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of EXAMPLE 1G (25 mg), dichlorobis(triphenylphosphine) palladium(II) (4.36 mg), phenylboronic acid (8.33 mg), 1M sodium carbonate (0.087 mL) and 7:2:3 dimethoxyethane/ethanol/water (1 mL) was heated in a microwave at 160° C. for 10 minutes. The mixture was concentrated and diluted with 1:1 dimethylsulfoxide/methanol. The solid was filtered, dissolved in N,N-dimethylformamide, cooled at 0° C. for 18 hours and filtered to afford the title compound. 1H NMR (DMSO-d6) δ 9.24 (d, J=2.1 Hz, 1H), 8.40 (dd, J=7.9, 1.2 Hz, 1H), 8.27 (d, J=8.2 Hz, 2H), 8.23 (dd, J=7.6, 1.2 Hz, 1H), 8.00 (s, 1H), 7.94 (d, J=8.2 Hz, 2H), 7.79 (d, J=7.0 Hz, 2H), 7.62 (t, J=7.8 Hz, 1H), 7.54 (t, J=7.6 Hz, 2H), 7.46 (t, J=7.3 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 1:1 dimethylsulfoxide/methanol
  3. filtrationThe solid was filtered
  4. dissolutiondissolved in N,N-dimethylformamide
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1e44c33d66aa491fa15bb2106e66507b
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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