Sodium Carbonate → HCID 21109358, compound

HRID 1766121Notes

Reaction equation

HRID 1766121 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[S:10][C:11]=2[CH2:12][OH:13])=[CH:4][CH:3]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1(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)C=CC=CC=1>[C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[S:10][C:11]=2[CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 17951834HCID 17951834, compound

Product 1

HCID 21109358HCID 21109358, compound

Reagents, catalysts & solvents 2

HCID 178420554HCID 178420554, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of [4-(4-Bromobenzyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methanol (0.33 g, 0.78 mmoles, 1 eq) in dry 1,2-dimethoxyethane (5 ml, 0.16M) was added tetrakis(triphenylphosphino) palladium I (0.45 g, 0.39 mmoles, 0.5 eq) and stirred for 5 minutes at room temperature. Phenylboronic acid (0.143 g, 1.2 mmoles, 1.5 eq) was then added followed by the addition of sodium carbonate (2M aqueous solution, 2.3 ml, 4.68 mmoles, 6 eq). The reaction mixture was heated at 100 degrees centigrade for 13 hours at which point, after cooling to room temperature, the reaction was partitioned between EtOAc and water. After separation of the phases the organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo to yield after purification by silica gel chromatography (CH2Cl2 to 2% MeOH/CH2Cl2) 268 mg (80%) of product.

Workup

  1. temperatureThe reaction mixture was heated at 100 degrees centigrade for 13 hours at which point
  2. temperatureafter cooling to room temperature
  3. customthe reaction was partitioned between EtOAc and water
  4. customAfter separation of the phases the organic phase
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield
  10. customafter purification by silica gel chromatography (CH2Cl2 to 2% MeOH/CH2Cl2) 268 mg (80%) of product

Sources & evidence

ORD record
ord-46d8801fcfb2479e8f104dc55be4d8b4
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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