Sodium Carbonate → N-(4-(2-(pyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

HRID 2056696Notes

Reaction equation

HRID 2056696 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:3]=1.[N:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C([O-])(O)=O.[Na+].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>[N:32]1[CH:37]=[CH:36][C:35]([C:2]2[N:7]=[C:6]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)[CH:5]=[C:4]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[N:3]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 58612070N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide

Product 1

HCID 11634832N-(4-(2-(pyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide (137 mg, 0.29 mmol, Example 7(d)), 4-pyridinyl boronic acid (40 mg, 0.32 mmol, Aldrich), Pd(PPh3)4 (24 mg, 0.02 mmol, Aldrich) and 2N Na2CO3 (0.5 mL) in 1,2-dimethoxyethane (1.5 mL) was heated at 125° C. in a microwave synthesizer for 20 min. The reaction mixture was cooled to room temperature, diluted with sat. aqueous solution of NaHCO3 (5 mL) and extracted with EtOAc (2×30 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (gradient 50-90% EtOAc/hexane) gave the title compound as a light-yellow amorphous solid. MS (ESI, pos. ion.) m/z: 508 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×30 mL)
  3. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel column chromatography (gradient 50-90% EtOAc/hexane)

Sources & evidence

ORD record
ord-e2120a1b1e0f442e9f5eaa7f2cc7e118
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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