Cesium carbonate → HCID 16221823, compound

HRID 1678467Notes

Reaction equation

HRID 1678467 reaction equation
[O:1]=[S:2]1(=[O:33])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:32]=[CH:31][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19](B4OC(C)(C)C(C)(C)O4)=[CH:18][CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Br[C:35]1[CH:36]=[C:37]([NH:42][C:43]([CH:45]2[CH2:47][CH2:46]2)=[O:44])[CH:38]=[CH:39][C:40]=1[CH3:41].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:45]1([C:43]([NH:42][C:37]2[CH:38]=[CH:39][C:40]([CH3:41])=[C:35]([C:19]3[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]4[CH:31]=[CH:32][C:9]([CH2:8][N:5]5[CH2:6][CH2:7][S:2](=[O:1])(=[O:33])[CH2:3][CH2:4]5)=[CH:10][CH:11]=4)=[CH:17][CH:18]=3)[CH:36]=2)=[O:44])[CH2:46][CH2:47]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 59822337HCID 59822337, compoundHCID 60402418HCID 60402418, compound

Product 1

HCID 16221823HCID 16221823, compoundYield 7.8%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl) -N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (70 mg), cyclopropanecarboxylic acid (3-bromo-4-methyl-phenyl)-amide (38 mg) in DME (4 ml) and water (1.5 ml) containing cesium carbonate (50 mg) and tetrakis(triphenylphosphine) palladium (0) (10 mg) was heated to reflux for 18 h. The cooled mixture was then partitioned between water and ethyl acetate. The dried extracts were evaporated and the residue purified on silica gel. Elution with 0-30% DCM:EtOH:NH3; 20:8:1 in DCM gave the title compound as a tan solid (6 mg)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. customThe cooled mixture was then partitioned between water and ethyl acetate
  4. customThe dried extracts were evaporated
  5. customthe residue purified on silica gel
  6. washElution with 0-30% DCM

Sources & evidence

ORD record
ord-5b0f3717dfe643b6bdf3843913c98678
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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