Ammonium Chloride → HCID 67065139, compound

HRID 547033Notes

Reaction equation

HRID 547033 reaction equation
[CH2:1]([C:3]([C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[C:29]([CH3:42])[CH:28]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:26])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:43][O:44][C:45](=[O:54])[CH2:46][C:47]1[CH:52]=C[C:50](Br)=[CH:49][CH:48]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+:64]>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.CN(C)C=O>[CH3:43][O:44][C:45](=[O:54])[CH2:46][C:47]1[CH:52]=[N:64][CH:50]=[C:49]([C:30]2[CH:31]=[CH:32][C:27]([C:3]([CH2:4][CH3:5])([C:6]3[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]4([O:21][Si:22]([CH3:23])([CH3:24])[CH3:25])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)=[C:8]([CH3:26])[CH:7]=3)[CH2:1][CH3:2])=[CH:28][C:29]=2[CH3:42])[CH:48]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 57709132HCID 57709132, compound

Product 1

HCID 67065139HCID 67065139, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

N,N-Dimethylformamide (2.0 mL) was added to 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cycloheptylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 128-(2); 64.4 mg, 0.110 mmol), (4-bromo-phenyl)-acetic acid methyl ester (30.2 mg, 0.132 mmol), tetrakis(triphenylphosphine)palladium (0) (12.7 mg, 0.0110 mmol) and potassium phosphate (35.0 mg, 0.165 mmol), and the mixture was stirred with microwave heating at 140° C. for seven minutes in a nitrogen atmosphere. An ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 85:15) to give the target compound as a colorless oil (27.0 mg, 46%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 85:15)

Sources & evidence

ORD record
ord-f33737d2caa74b2ba446b1946606c3d1
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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