1-Bromo-4-tert-butylbenzene → HCID 58576748, compound

HRID 511196Notes

Reaction equation

HRID 511196 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 775951-Bromo-4-tert-butylbenzeneHCID 634876Binap, (A+-)-2×HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 58576748HCID 58576748, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-bromo-4-tert-butyl-benzene (639 mg; 3.0 mmol), [1,4]diazepane-1-carboxylic acid tert-butyl ester (500 mg; 2.5 mmol), tris-(dibenzylidenacetone)-dipalladium (0) (45 mg; 0.049 mmol), sodium tert-butoxide (360 mg; 3.75 mmol) and (±)-2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (92 mg; 0.147 mmol) is added toluene (5 mL) and the resulting mixture is irradiated in a mono-mode microwave oven for 2 hours at 100° C. Further tris-(dibenzylidenacetone)-dipalladium (0) (45 mg; 0.049 mmol) and (±)-2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (92 mg; 0.147 mmol) are added and microwave irradiation at 120° C. is continued for another hour. The reaction mixture is then diluted with ethyl acetate and filtered. The filtrate is concentrated under high vacuum and the obtained residue is purified by column chromatography on silica gel (hexanes/dichloromethane 50:50 v/v to 100) to afford the desired compound (284 mg; 0.85 mmol).

Workup

  1. customthe resulting mixture is irradiated in a mono-mode microwave oven for 2 hours at 100° C
  2. custommicrowave irradiation at 120° C.
  3. waitis continued for another hour
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under high vacuum
  6. customthe obtained residue is purified by column chromatography on silica gel (hexanes/dichloromethane 50:50 v/v to 100)

Sources & evidence

ORD record
ord-72cedb0b2a0f4a718ebda23901efab03
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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