Sodium Carbonate → HCID 86599799, compound

HRID 1374801Notes

Reaction equation

HRID 1374801 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[C:5]([CH3:15])[N:6]2[CH2:11][C:12]([OH:14])=[O:13].ClC1C=CC(S[C:32]2[C:40]3[C:35](=CC=C[C:39]=3I)N(CC(O)=O)C=2C)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[C:53]1(B(O)O)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(O)C.C1(C)C=CC=CC=1.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>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:16][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[N:6]([CH2:11][C:12]([O:14][C:40]([CH3:35])([CH3:32])[CH3:39])=[O:13])[C:5]=2[CH3:15])=[CH:18][CH:19]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10047207HCID 10047207, compoundHCID 10344116HCID 10344116, compound

Product 1

HCID 86599799HCID 86599799, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of the product of example 22 part (ii) (0.5 g) in ethanol (0.8 ml) and toluene (3 ml) was added 2M sodium carbonate solution in water (1.4 ml), phenylboronic acid (0.131 g) and tetrakis(triphenylphosphine)palladium(0) (1.2 g). The reaction was heated to reflux for 2 hours, cooled and concentrated in vacuo. The residue was purified by flash column chromatography to give the sub-title compound (0.4 g). This was used in step (ii) without further characterisation.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1a8571ad6a3647ba82878a9704dff40c
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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