Potassium Carbonate → 4-{5-Cyano-7-[(1Z)-1-methylprop-1-en-1-yl]-1,3-benzoxazol-2-yl}-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

HRID 2093636Notes

Reaction equation

HRID 2093636 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([C:37]#[N:38])[CH:3]=1.[CH3:39]/[C:40](/B(O)O)=[CH:41]/[CH3:42].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[C:37]([C:4]1[CH:3]=[C:2](/[C:40](/[CH3:39])=[CH:41]\[CH3:42])[C:10]2[O:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:20][CH2:21][N:22]([C:25]5[N:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:28]=[CH:27][N:26]=5)[CH2:23][CH2:24]4)=[O:16])=[CH:35][CH:36]=3)=[N:7][C:6]=2[CH:5]=1)#[N:38]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11389361(E)-But-2-EN-2-ylboronic acidHCID 687430814-(7-Bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

Product 1

HCID 687875624-{5-Cyano-7-[(1Z)-1-methylprop-1-en-1-yl]-1,3-benzoxazol-2-yl}-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

Reagents, catalysts & solvents 3

HCID 178454861HCID 178454861, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide (30 mg, 0.051 mmol), [(1E)-1-methylprop-1-en-1-yl]boronic acid (18 mg, 0.18 mmol), potassium carbonate (3M solution in water) (150 μl), and 1,1′-bis(di-t-butylphosphino)-ferrocene palladium chloride (2 mg, 0.0031 mmol) in tetrahydrofuran (5 ml) was heated at reflux overnight. The mixture was diluted with ethyl acetate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to afford the title compound. Mass spectrum (ESI) 561.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-340f26044f2c4bbf871ee29a66514056
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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